


Legally Yours

by smolandgrumpy



Category: Supernatural
Genre: Angst, Blackmail, Denial of Feelings, Dirty Talk, Dry Humping, F/M, Fake/Pretend Relationship, Feelings Realization, Fluff, Oral Sex, Praise Kink, Protective Dean Winchester, Public Sex, Semi-Public Sex, Slow Build, Slow Burn, Smut, Soft Dean Winchester, Vaginal Fingering
Language: English
Status: In-Progress
Published: 2021-01-01
Updated: 2021-03-10
Packaged: 2021-03-11 02:34:44
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 22
Words: 95,301
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28217805
Author URL: https://archiveofourown.org/users/smolandgrumpy/pseuds/smolandgrumpy
Summary: Dean Winchester tops the list of hottest entrepreneurs 2020 and yet, there’s still something he wants but can’t have because, in order to get that, he would have to settle down and get married. She agrees too quickly because she wants to secure a more comfortable life for her and her daughter. Will she be able to help Dean get what he wants without losing herself in the fake story they spin up to deceive his father and the world?
Relationships: Dean Winchester/Reader, Dean Winchester/You
Comments: 221
Kudos: 183





	1. Chapter 1 - Prologue

Y/N’s sitting at her desk as she types an answer to the inquiry from a customer, when her friend Donna practically slams a glamour magazine over her keyboard. 

“Have you seen this?” The blond woman asks. 

“Jesus, Donna! I haven’t saved that document yet! God!” She picks the magazine up and tosses it to the side as she continues to finish the document on her screen. 

Donna’s still waiting, staring at her and she wonders if that woman has nothing else to do. Y/N’s sure Donna has plenty to do, they always have a lot of work and that’s why she gets home so late and sometimes, Liv would already be asleep. Sometimes, when she’s lucky, Liv was awake and she’d read her a bedtime story of princesses who are rescued by a heroic prince.

As soon as Y/N is finished, she turns around in her chair, to see her friend still staring at her instead of doing her own work. 

“What is it?” She asked with that added annoyed nuance to her tone of voice.

“Look!” Donna lifts her chin to point towards the magazine she slammed in front of Y/N just a moment before, “Have you seen it?”

Turning back around to her desk, she picks it up, “Donna, I’m not reading those mags, so no, I haven’t seen it. Why?”

Instead of answering her, Donna only grins. The grin that shows her dimples. The wicked one, “Page twenty-six,” 

With raised eyebrows and that little spark of curiosity which Donna had added to her interest, Y/N rifles through the pages until she reaches page twenty-six. 

There’s a picture of a man who stares right at her. He’s wearing a perfect suit. His one hand fakes the adjusting of his cufflink on his wrist. It’s a total male model pose. Well, he looks like one, so she can’t really say that anything’s out of the ordinary. 

At a second glance, though, she realizes that he looks familiar. His face is a little scruffy, but that makes him look edgier, makes him look more handsome. He’s smiling bright, showing his perfect white teeth. There are crinkles around his emerald eyes, seven on his right side, and she knows she shouldn’t even be counting them, so she ignores his left side. And she definitely can’t help but notice the freckles across his face. 

_ Oh _ , she thinks.

_ Oooohhhh. _

“Is that..?” She asks with a frown that gets deeper between her eyebrows because she’s just not sure? She hasn’t seen the man that many times in real life. 

“Ya! Our fucking boss! The icy King!” Donna shouts, “Isn’t he dreamy? My god, I wanna eat him up! And he doesn’t look as icy and distant like he always does,”

“Donna!”

“What? Only telling the truth here! Read what the headline says!”

Her friend is right, though, Mr. Winchester’s normal aloof and cold persona isn’t captured in the picture. He’s known to be the icy King in the company. Instead, he looks kind of welcoming and warm. Y/N eyes go to the top of the page, and she can’t lie, it’s hard to concentrate on the writing when there’s a good looking man staring her down.

The headline is in all caps.

> _ DEAN WINCHESTER, HOTTEST ENTREPRENEUR 2020 _

She frowns, as her eyes leave the magazine to look back at her friend, “ _ That’s _ what you wanted to show me?” 

“Duh! There’s also a whole article about him being the center of attention everywhere he goes,”

“Well, that’s not really surprising, is it? Looking like that?”

“It also says that he has a fiancée.”

“That’s also not surprising,” Y/N shrugs, “I mean, seriously, look at him. Who wouldn’t want to marry that?” She didn't. At least not when they say that he’s cold-hearted. But again, she’s not the norm here because every female is gushing about him. 

She closes the magazine loudly, deciding that she shouldn’t waste more time. She wants to get home on time today. Liv went on a field trip with her school and she wants to hear her little girl telling her about how exciting it was. Y/N still has a lot of work to do and also a meeting with her supervisor later. The sleazebag.

“So, can I go back to work?” She turns to Donna, “I have a meeting with Raphael in about twenty minutes.”

“Ew,” Donna cringes her nose.

Y/N rolls her eyes, “Exactly,”

“Will you tell him off?”

“I already did,” She sighs, “Multiple times,”

“Why don’t you just go to HR?”

Donna knows what happens. What  _ always  _ happens when she has a meeting with Raphael. He’s always trying things with her. Accidentally brushes his hand against her breast or her ass. He once told her to sit in his lap as he was showing her the numbers of her performance. It wasn’t the first time he suggested it, and she doubts that it will be the last time either. He tried to kiss her more than once, but knowing that they are in an office environment, he didn’t dare to force her too much. He also offers to drive her home almost every week, and she’s slowly getting tired of it, not to mention creeped out.

At their last meeting, he made her hang up a picture frame in his office. His hand rested on her hips to supposedly  _ support  _ her, but they traveled further down until he kneaded her ass in his palms. She immediately got down from there, and left the room wordlessly. 

She knows another secret about Raphael, though. One she could use against him, but she just doesn’t know how just yet. Y/N knows and has got proof that he’s been skimming money. He takes it out of the customer’s account. Not a lot, a small sum that customers wouldn’t notice is missing, but in the end, it’s probably a whole lot when he does it to all the customers he’s supposed to look after. 

Again, she can’t really bring that up because she’s sure that he’ll spin it around and Raphael is good at that. With a push on the button of his keyboard, he could reverse everything and she knows that. 

“I can’t go to HR,” Y/N lowers her head and mumbles to her friend, “Because they won’t believe me,”

And that’s the truth too. The Head of HR is Duma, a woman who occasionally fucks Raphael. They have a friend with benefits thing going on, even if she’s married with children. Duma will never believe her because Y/N’s sure that Raphael can spin this perfectly to fit his narrative. 

Besides, what can she possibly tell? It’s her against him. It’s like a mouse against an elephant. She’s only an accountant and is replaceable, whereas Raphael is a member of the leadership team. And who will be let go? She doesn’t think it’s going to be him and she  _ needs  _ the job to survive. 

Y/N watches as Donna’s lips start to curl up, the white teeth of the woman are visible, as she drums her fingers annoyingly on her own desk.

With a frown, she asks her friend, “What?”

“I have an idea,” Donna says and pulls up her outlook calendar. 

She types in something, and then a calendar appears with a lot of colorful blocks. 

_ Oh no _ . She has quite the idea of who’s calendar it is even if she can’t read the name from where she’s sitting, which is too far away because she doesn’t want to give the impression that she’s not working. And it’s stupid that they can do that. They have quite an open calendar policy at the office. Everyone can send and block meetings for everyone, even for the icy King. 

“Donna, no!”

“Why, Donna, yes!” Her friend grins, “He has an open window right now. The meeting in the boardroom is in ten minutes. You should go tell him what you know. If someone can change anything, it’s him, right?”

Donna’s not wrong, she isn’t. But Mr. Winchester is what? At least four tiers above her if not five. Why should he care what a simple worker in his company is thinking? Why should he care what the hell she goes through every day while he earns enough profit to fuel his expensive and glamorous lifestyle?

“He wouldn’t believe me,” She shakes her head.

“You can tell him about the money skimming, I bet he won’t be happy to hear that.”

“Ugh,”

Donna stands up and walks over to her, braces her hands on the chair Y/N’s sitting on, “What’s the worst that could happen, huh?”

“That I get fired?”

“Meh,” Donna squeaked, “I doubt that. You’re doing a great job. Your records are great. And besides, if they do that, you can go and file a lawsuit against them. Besides, who knows, if you go to HR, Raphael will fire you before the icy King does.”

True, but still. 

“Now go get your ass up to the executive floor. Maybe take him a coffee, I heard he likes it black,”

“Oh, just like his heart?”

“Ya, maybe I wouldn’t tell him that?” Donna chuckles.

  
  
  


*

  
  
  
  


Y/N’s on her way to the elevators. She can’t believe that she’s really doing it. But Donna’s right. She can’t go on and live like that. It’s already hard to part from her child every morning and to get bullied at her job and being sexually harassed should not be the norm. She just fucking wants to earn enough money to keep her kid and herself above water.

God, she’s really doing it! 

_ Fuck. _

There are six elevators lined up in the foyer. Three on each side. Only one goes up to the executive floor and also one is reserved for Mr. Winchester’s penthouse on the top floor. Everybody knows that. 

To get the elevator to run up to the executive floor, Y/N would need to have a card with a chip, which she doesn’t, and she feels stupid to have just realized it. And now she’s standing here, lost, with a hot black coffee in a lidless plastic cup that almost burns her fingers off.

_ Ugh.  _

She’s so fucking stupid.

Well, she could still try, couldn’t she? She jumped over her own fear and has come this far. She definitely shouldn’t give up now. 

Her finger hovers over the buttons. Closing her eyes and exhaling loudly, she gives the button a push. Standing back, she waits, her heart is drumming loudly against her ribcage.

And she doesn’t even have to wait long because not even thirty seconds later, the elevator dings and opens up to reveal a man in a nice suit staring back at her.

_ It’s him. _


	2. Chapter 2

_It’s him._

Y/N’s heart picks up its pace and she feels something twisting in her gut. 

_Oh god, don’t pass out now, Y/N, for god’s sake!_

The man who stares back at her is Mr. Winchester. 

Jesus, she wasn’t prepared for this. 

She was prepared to see him in the meeting room, but not in the elevator? Like, she can’t possibly ride up with him, can she? He’ll wonder why she is going up there and it would look completely stupid if she trails behind him to the meeting room. He’d ask her why she’s here and… Fuck, she’s just not prepared for that right now. All the images and scenarios she spun in her head was of her meeting him up there, not in the goddamn elevator! 

It doesn’t fucking help that he looks even better in real life. How is that even possible? It’s not fucking human and it is certainly not fucking fair. 

Y/N must have been staring at him for too long because the elevator doors start to close. Mr. Winchester quickly takes a step forward and braces his hand at the door, preventing them from closing right in front of her nose. The doors open up again and she’s still there, unable to do anything else but stare at him wordlessly.

Mr. Winchester leaves his hand there and continues staring at her with those piercing green eyes that look a bit troubled. They look clouded, tired. They aren’t as sparkly as the picture she saw in the magazine. 

She wants to move, she really wants to, but it’s like her feet are taking root on that damn marble flooring.

“You coming?” Mr. Winchester asks with a raise of his one eyebrow. 

_Talk, Y/N! Fucking talk!_

“Yeah,” She manages to push past her lips and is surprised that she managed to utter a coherent word at all.

“Okay, then you should come now, or I’ll be late,” Mr. Winchester nods his head and moves away from the doors to make space for her.

In her mind, she’s already moving, but apparently, she isn’t because Mr. Winchester asks again as he moves and braces his hand on the elevator door, preventing it from closing once more, “You sure you’re coming? Because I’m not holding that door open a third time,”

“Uh, yeah… Yeah!” 

Finally, she wills her limbs to move and slips into the confined space. The door’s already closing and catches the elbow of the arm she holds that fucking cup of coffee, sends it spilling over the edge and onto Mr. Winchester’s expensive-looking leather dress shoes.

_Fuck._

Now she’s in the elevator. With him. And she ruined his shoe.

This is great.

“Shit, I’m sorry, sir, I didn’t mean to do that,” She stammers as she backs up against the elevator wall, feeling the need to be as far away from Mr. Winchester as she possibly can.

Y/N expects him to yell at her, expects him to be mad, maybe to tell her to get lost, but instead, He fishes a handkerchief out of his suit pocket and bends down to clean up his shoe. 

Meanwhile, she’s spiraling, mutters _sorry_ way too many times.

When Mr. Winchester stands back up, he slips the handkerchief back into his pocket and frowns at her, “Can you please stop apologizing? You’re hurting my head.”

“‘M sorry,” She mumbles again and lets out a loud exhale.

“You just did it again,”

“I’m sor— shit!”

Mr. Winchester chuckles. He fucking chuckles. 

“Next time, put a lid on your coffee, alright?”

“Uh,” She starts to say, but then the elevator dings and signals that they have arrived on the executive floor. 

He doesn’t wait for her, starts to walk out and all she can do is follow.

“Mr. Winchester, wait,” She says. There were people walking around past them, hurrying from one meeting room into the other. He turns around to face her, raises that one eyebrow again.

“What is it?”

“This coffee was actually for you,” Y/N says and holds it out to him, “I was hoping that I could talk to you about something,” 

“Yeah?”

“Yeah,”

He nods before he takes the coffee from her hand and takes a sip before letting out a sigh of satisfaction. Smacking his lips, he nods again, “Yeah, black like my heart, thanks. So listen, if you want to talk, you gotta keep up with me because I’m going to be late,”

Before she can ask him what he’s talking about, he turns around and walks away, leaving her to hurry after him to catch up.

“I just need a minute,” She says, almost out of breath. His legs are so damn long and hers aren’t. 

“You see the people in there?” He looks straight ahead at the board meeting room where people were already sitting or standing around, waiting for him. She can see it clearly through the glass walls, “They are all waiting for me. I have a meeting and you have to wait. No,” He tilts his head to look down at her, “In fact, I want you to join me so when someone asks why I’m late, I let you explain that it was you who couldn’t decide if the elevator I was good enough for you.”

_Fuck._

“But—”

She wants to continue speaking, but they have already arrived at the meeting room and all eyes are on them. 

Mr. Winchester opens the door one-handed, in his other hand he’s balancing the coffee she brought him.

“After you,”

Y/N nods in defeat and walks in, moving to the furthest corner where some other suits are standing because they aren’t important enough to take a seat. If someone notices that she doesn’t belong here at all, they didn’t let on. 

Placing his coffee at the head of the table, Mr. Winchester greets everyone and soon starts with his presentation. There’s a big screen behind him, showing the figures from last month.

Everything seems so natural for him. The way he talks compels everyone to listen. His voice is deep, gravelly, the kind of soothing voice that makes people feel at ease, including her. It’s a voice she’d like to hear reading to her. Mr. Winchester should definitely think about doing a podcast, or record a fantasy novel, maybe erotica. She starts to feel the blood rushing to her cheeks thinking about him reading an erotic novel for her to listen to. She smirks and shakes her head, tries to get the indecent thoughts out of her mind. 

When she composes herself, she watches him some more. She can only see the back of him and that’s definitely not bad to look at. His shoulders are broad, and even with the suit jacket, she can see his back muscle shift as he points out the numbers. The jacket rides up, exposing his pert ass. 

God, she’s feeling warm again. 

There’s an aura surrounding him. It feels like when he moves, the whole world shifts with him. 

She’s still looking at his back when Mr. Winchester suddenly turns around. His eyes are on her and she feels like he just caught her with her hands in the cookie jar. Lowering her head, she bites on her lip.

After a brief meeting, everyone starts to walk out, leaving only a handful of people still in there. Mr. Winchester takes the cup of coffee she brought him, brings it to his lips, and drowns it in one go. He walks over to the trash can and tosses the cup away. Turning around, he looks at her again and there’s something uneasy about him. If she thought that he looked tired before, he is looking exhausted now. 

Seeing him like this has her worried. She’s always been empathic and there’s that feeling she gets in her gut, the feeling of caring and she genuinely wants to know the reason why he looks so tired.

“Are you okay? You look tired,” 

As soon as the words are out, she clasps her hand over her mouth. She didn’t mean to say them aloud.

People were speaking in hushed voices before, but it’s gone completely silent now.

Before she can say that she’s sorry, Mr. Winchester's eyes narrow back to their original size after having widened upon hearing her words. To her surprise, his lips curve into an easy smile.

“Yeah, sweetheart, I’m okay. It has just been a long night,” He says as he walks along the table to the back where she’s standing. He comes to stand right next to her, weaves an arm around her waist, and pulls her close until the side of her arm is pressed against his firm chest. 

He whispers in her ear, low and deep, words only she is supposed to hear, “Please, play along,” He places a kiss on her temple, making her heart jump. 

He chuckles before he turns back to face the room. With that easy grin still on his face, he turns back towards her, places another kiss on her heated cheek and speaks again while he looks at her. This time, his voice is louder, “How was your visit to your relatives?”

Her cheeks feel like they are burning and there is the pricking of his scruff against her sensitive skin. She noticed something she had before, but she was not sure because the smell of coffee overrode it in the elevator but damn, she smells it now. Mr. Winchester smells absolutely delicious. His cologne suits him. It has something dark about it. She needs to focus to not get lost in the smell of him.

Mr. Winchester squeezes the hand that’s around her waist. The tip of his fingers dig a little into her sides. It’s a reminder for her to come back to reality.

“Oh,” She breathes out, “It was fine. I’m glad to be back, though.” She lies with a fucking straight face. She absolutely hates to lie, is probably not very good at it and she’s afraid that it’ll show.

A loud cough comes from the chair right next to where Mr. Winchester was standing moments before, and a graying man stands up. The man quickly does up the buttons on his suit jacket before he walks over to them. The other executives seem to know that they don’t belong and finally the last of them leave the room soundlessly. 

“Who’s this woman?” The older man asks.

“Dad, I don’t think I have introduced the two of you yet. This is my financée,”

She’s about to nod and introduce herself like Mr. Winchester wants her to play along, but there’s another squeeze and he quickly steers her towards the door.

“Dean, I need to have a word—”

“—I’m sorry, we really need some alone time now, as I haven’t seen her for a couple of days. I’ll introduce the two of you some other time. You can schedule a meeting with us.”

All she can do is smile self-consciously in passing, nodding as she goes, but she doesn’t miss the glare of the older Mr. Winchester. 

Quickly, Mr. Winchester pulls the door open and gives her a light push to the small of her back. 

“I’ll see you, Dad,” Mr. Winchester sends him a courtesy nod before he walks out behind her.

As soon as they are standing outside of the room, he takes her hand, pulls her along the hallway, and ushers her into his office.

  
  
  
  


_______________________________________________________

  
  
  
  
  


Dean lets go of her hand and pushes her into his office, closing the door behind him gently. He watches her walking in further, probably taking in the spacious room that he’s rarely in anyway. 

He rubs his hand over his face, pinches his eyes. God, he’s really exhausted. 

Leaving her standing in the middle of the room, he walks over to his desk and leans his backside against, crossing his arms over his chest. 

“We need to talk,” He says simply, his thumb brushing at his chin. The sound of his skin against his scruff is loud in the room.

“Duh! Yeah,” She raises her eyebrows and signals with her hand. He’d think it’s cute would the circumstances be different, “What the hell was that?”

It blurts out of her and then Dean watches as she cringes, seemingly regretting her outburst. 

“With all due respect, sir,” She starts again, her voice a little shaky, “Don’t you think everyone who heard it has already found out that I’m not your fiancée? Because I’m really not.”

His lips curve into a grin, that cocky one he’s known for. Dean raises his one eyebrow, “Would you like to be?”

“What?”

“I’m asking if you’d like to be my fiancée,” Dean says it with a straight face. He’s good at that and he can understand why it might throw people off. He’s good at that too.

She throws her hands in the air and lets them drop down by her side as she sighs loudly. After a second, she composes herself, “Sir, the only reason I’m up here is to talk to you about my boss. I’m only a simple accountant working on the 10th floor.”

Dean shrugs, “Not anymore,” 

He makes his way around his desk and sits down in his chair. His hands are on his keyboard, typing in his password and opening the employee database. 

“I’m promoting you,” Dean says as he pulls up her data. She might not know this but Dean knows exactly who she is.

She frowns at him, as she walks closer, “Sir, I didn’t come up here for a raise. I’d really like to talk to you about Raphael Barnes, my supervisor, sir.”

Dean pulls up the profile of Raphael Barnes. It contains a lot of red flags from other HR complaints, but they seem to have been overruled by the head of HR. All of them quashed Duma. Guess he has to get rid of two people, huh? These types of accusations do not come out of nowhere, at least not this many. Dean’s not a fool, he knows his business and he certainly knows when something doesn’t look right. 

“Sir?”

“Please, call me Dean,” With a click of a button, Dean pulls her information back up. He looks at her with that signature raised eyebrow, “Your name is Y/N, right? Y/N Y/L/N?”

Her lips open and close, “How do you know?”

He chuckles, “I know who I employ. I have a good memory. Every month, I get a summary of new employees and their photos sent to me,”

Leaning back in his chair, he looks at her. He can see that she feels uneasy. There’s clear irritation on her face, but she shakes her head, as if she wants to compose herself.

Letting out a breath, she looks at him, “Okay, let’s start anew. I’m here because I have a complaint. I’m sorry I snuck up here, and I know I should have made an appointment, but it’s important,”

“What did he do?”

“Uh..,” She begins and Dean can see that it makes her feel uncomfortable. He swears if that Raphael dude touched her, he’ll be dead meat. Dean does not tolerate any form of sexual harassment under his fucking roof. 

“Y/N, what has he done?” He clicks a button on his keyboard before he stands up. In the distance, the printer starts to come to life. Slowly, he makes his way around the desk back to where she’s standing.

“He’s been skimming money,” She says, but she doesn’t look at him, her gaze trained on her toes. 

“There’s something more, right?”

Like, yeah, skimming money is enough, but he can’t shake the feeling that there’s something more to it. Something she doesn’t tell him.

“Yeah,” 

Dean nods. He understands. 

“Right, he’s fired. And I’ll fire Duma too, because it seems like she’s in it from the way I see it.”

She is finally looking at him now, but she frowns, “You firing them? Just like that? And you’re not firing me?”

“Fire you?” Dean chuckles, “No, I have a proposition for you.” He says it with a straight face, showing her that he’s not kidding.

The frown doesn’t ease on her face though. Instead, it etches deeper into her skin and it’s weird but he kinds of want to reach out and rub it away. 

“Sir,” She starts, but stops, “Dean,” Y/N says again, using his name as he told her to. It sounds great out of her mouth, “You don’t even know me. You don’t even know if I’m telling you the truth!”

Dean starts to chuckle again at her outrage. She’s cute, he can’t deny that. And well, her suspicions might be wrong, but Dean was always good at reading people. It’s what this business is built upon. He’s never wrong and he can tell by how she behaves that she’s telling him the truth. 

Instead of elaborating and clearing her suspicions, he smiles, “So, let’s focus on the task at hand, shall we? How does $2,000 a day sound for you?”

“Two— what? For what?”

“Being my fiancée and eventually, becoming my wife.”


	3. Chapter 3

_ What? _

_ He’s kidding, right? _

“Is there a camera? Am I in some kind of a prank show?” Y/N looks around the spacious office nervously because he couldn’t possibly mean that. And if it’s a joke, it’s not a fucking good one.

Dean’s laughing, throwing his head back, holding his belly and all.

She frowns. It seems like frowning is the only thing she has done since she stepped foot into his office, that’s ridiculously huge. There’s a leather sofa in the middle of the fucking room and his desk set next to the floor to ceiling window. The view is magnificent. There’s a bookshelf taking up the whole right wall and a minibar with spirits and tumbler glasses sitting nearby, and a black box which, she assumes, probably contains ice cubes. The company policy doesn’t allow alcohol in the workspace but she guesses that doesn’t apply to the big boss.

Y/N wonders how much time he actually spends here, wonders how many books on the shelf he even touched.

When Dean composes himself enough, he shakes his head, and she still thinks it’s not funny. Y/N still thinks it’s a bad dream. Maybe she’ll wake up in her bed soon?

“No, I really mean it. There’s no camera in here,” He says with a satisfied smile.

Her mouth opens and closes as she tries to push something past her lips. It doesn’t come out at first but then it seems to just fall out, “Mr. — Dean, I am not a prostitute.”

The laugh that comes from his throat is louder this time. And he even brushes a tear away from his eyes. 

Dean’s hand goes up to his armpit as he gestures down his body, “Y/N, do I really look like someone who has to pay for women?”

“Uh…”

“Exactly, I don’t need a fucking prostitute. I need a wife.”

_ God _ , how can someone say that with such a straight face? It sounds fucking ridiculous, and the fact that he needs a wife sounds even worse than needing a prostitute, to be honest.

She stares at him, “You’re not serious.”

Dean chuckles, “I’m afraid I’m super serious,” 

He places both hands into his pants pockets and leans back against his desk and she doesn’t know how but he looks even more tired now. Like he hasn’t had any sleep for days, if not weeks. There’s that feeling in her gut again, something that prompts her to want to know that he’s okay, but she bites back her comment. It’s not the right time, nor is it the right place. 

Dean clears his throat before he goes on, “I don’t know if you’re familiar with tabloids,”

Her eyebrows knit together. The magazine Donna showed her today was the closest glimpse of tabloid that she has gotten in maybe years. Y/N just really doesn’t have time for that.

It seems like Dean can read her mind because there’s a smirk on his face, “Yeah, I thought so,” He shakes his head, “If you knew the tabloids, you’d know that I have, or rather had, a fiancée,” 

Y/N’s mouths open to speak because yeah, she remembers now. If he has, or had, a fiancée, why does he need her? Dean stops her with one raise of his index finger and her mouth closes. 

“She’s still on her way back from Mexico where she has spent a week fucking some noname male model slash actor,” He says as he lowers his chin, “It’s over between us and I need a replacement,” 

Oh, wow. That hurts a little. Like she’s a backup. An understudy. She’s not even a good one.

Not waiting for her thoughts to clear or to voice her opinion, Dean walks to the printer and grabs several pages from it before walking back to her. 

There’s a smile on his face as he checks if the pages are complete, “I had my lawyer write up a standard confidentiality agreement. You’ll find your benefits here, and there are clauses about expectation and your role in it.” He walks to the couch and spreads the contract on the little table in front of him, motions for her to join him. When she sits down he goes on, “The duration of the contract is pretty hard to determine, but you’ll be compensated for the inconvenience.”

Dean takes out the pen from his suit pocket and lays it on top of the first page, “Sign on the last page and I need your initials on the bottom of every page.”

_ What? _

_ Now? _

_ He wants her to sign it now? _

Y/N nibbles on her lips as her mind tries to make sense of all the things he’s said. He can’t really mean it, right? Why her? He could have anyone? She doesn’t know who his ex-fiancée was, but she bets she’s a fucking stunning woman that dresses nice, while her shirt comes from H&M and she only bought it because it was on fucking sale.

When she looks up at him, she realizes that he’s been watching her the whole time. His gaze is confident, expectant. An air of bravado surrounds him.

“Why did you choose me?” With one hand she brushes the hair back that falls around her face, tucks it behind her ear. It’s what she does when she’s nervous and right now she is. But she doesn’t know why. Maybe she’s afraid to hear the truth? “You don’t know anything about me. How are you so sure people would buy into the lie?”

Dean frowns at first, but then his lips curl up into a shy smile. He also moves closer. Their knees touch, “You asked me if I was okay.”

“Yeah? And?”

“In that moment, I could see that the answer really mattered to you. Like you are genuinely curious and somehow I had the feeling that you really cared to know if I was okay.”

He’s not wrong, but still.

“You made your decision based on me asking you if you’re okay?”

“Yeah,” He smiles and when he does so, she can count the crinkles around his eyes, “It seems to me like my answer would really matter to you.” There are still seven crinkles around his right eyes. She quickly ignores the left one because Dean continues, “You know, I think that if you can pretend to care so much about someone you barely know, you certainly can pretend to be my fiancée.”

She feels her cheek starting to get warm and Dean’s gaze doesn’t help so she quickly turns away, looking back to the contract on the little table. 

“I wasn’t pretending,” She mumbles, “You really do look tired,” And then she risks a glance back, “Are you okay?”

His smile doesn’t falter and he shrugs, his shoulders moving up and down, “I’d feel better knowing that someone who genuinely cares about other people would take my job offer,”

“You sound like you’re so sure about it,”

“It’s because I am,” Dean nods his head and there’s a satisfactory smile, “I’m never wrong. I think you showed me that you care and I believe that you’re the kind of person I can trust with the more intimate part of my life.”

Did he just say intimate? She frowns but swallows down the question that’s burning on her tongue. 

Instead, she asks, “Why do you need a fake fiancée at all?”

Yeah, because she still can’t wrap her mind around it.

Dean leans back on the couch before he lets out a sign. His hand goes to his hair, ruffles it up before he pinches the bridge of his nose.

“To buy me time until my lawyers can find a way to get the shares without being married. You’ve met my dad,” He starts to say and she nods, “Yeah, he owns a huge portion of the shares in the company.”

_ Oh. _

He continues, “The only way he will sign the shares over to me is when I settle down and marry. He doesn’t like my lifestyle, thinks it doesn’t fit the company’s values.”

“That lifestyle being?”

“Being single, I guess,” Dean shrugs.

“I don’t understand,” She frowns, “What will marriage change?”

There’s a chuckle, and Dean braces an arm over the back of the couch. His hand almost touches her shoulder, “Marriage will make people respect me more. They’ll know that if they invest in my business it’s not to fuel my lifestyle. The tabloids will stay away and won’t brand me as an eligible bachelor.”

That, she gets. 

“I understand,” She nods. 

“But that’s not all,” He leans his head on the couch as he watches her sideways. Like that, he looks pretty much relaxed. There’s a boyish charm around him, something she’s never seen before. He looks almost cute.

“It’s not?”

“No. I’m an only child. He wants to make sure that the family business doesn’t die with me.” 

Her eyebrows climb up her forehead, “Well, I don’t think I’m going to help you with that,”

Dean snorts out a laugh, “I know. It’s on the second page of the contract.”

She moves away from him and inches closer to the edge to look at the second page. While she reads, he speaks behind her, “There’ll be minimal physical contact apart from the time when we have to keep up the illusion. No sex.”

“Oh, thank god,”

“You don’t have to be so happy about it,” 

She turns around to see that he’s frowning. There’s also the raise of one eyebrow.

Her eyes travel over his body. Even when he sits he looks so damn pretty and attractive. Maybe she should ask about that clause? Because it seems stupid. Well, she might not really want it  _ now _ , but what if she does want it later? She can’t lie, he looks delicious.

It seems like he notices her inspecting him and instead of saying a word, he replicates her treatment. His eyes roam over her body. His gaze feels hot on her skin. 

“What if we change our minds later?”

“Change our minds about what?”

“Uh, about the physical contact,” She can’t even say it without feeling her ears burning. 

Dean raises his one eyebrow as his lips curl into a cocky grin, “Changing our minds about having sex, you mean?”

God, does he have to say it like that? It sounds so hot coming out of his mouth. But basically, yeah.

She nods her head, “I’m a woman, you’re a man. Maybe I like to be touched every now and then.”

His smile turns amused as he leans over and scribbles something on page two and strikes out some other things, “There, the clause will stay open.”

“As simple as that?”

“Yeah,” He grins and there’s a sparkle in his eyes which she hadn’t seen before. It’s like he’s really relieved, like a weight had been lifted off his shoulders.

But then something shifts, she can feel it in the air around her. His eyes turn back to ice, even if it’s just for a moment. 

“After our marriage, my dad will sign his shares over to me. If we even have to go that far. My lawyers are working right now to find that loophole, so maybe this will be over before we know it. If we still have to get married, I want you to remember that it’s not real, okay? Everything about this is fake. I’m paying you quite a large sum to be my wife, don’t make me regret this.”

He’s not even wrong. And god knows she can use the money so much. She could move out into a nicer neighborhood, she could set money aside for Liv’s education. Her life will improve significantly.

But there’s something nagging in the back of her mind. 

She takes the pen, but she looks at him before she signs, “Can I ask you something?”

“Yeah,” 

“What will happen if you fall in love with me?”

There’s a throaty laugh that he pushes past his lips, as if her question is really fucking funny, but when he sees that she didn’t intend for it to be taken as a joke, he frowns.

“Sweetheart, you think that will happen?”

“I don’t know what I think,” She says, and it’s the truth, “Fact is that we're going to be spending a lot of time together and we’ll have physical contact in public and I don’t know. It is normal for sparks to fly.”

What she actually means but doesn’t say, though, is that the chance of her falling in love with him will actually be much greater than the other way around.

Dean nibbles on his bottom lip, as if he really thinks about what she’s saying and after a couple of seconds, he shakes his head, his thumb goes to his brow, scratches at it, “I don’t think it’ll happen. I’ve never been in love, not even when I really wanted to be.”

_ Ouch _ . She doesn’t know why but that hurts. 

“Have you?” He asks.

And it catches her off guard. But she composes herself and shakes her head, “No,”

Which is the truth. She wished she would have been once, but even what she felt back then with Jimmy, that wasn’t  _ love _ .

“There we have it. It will be more unlikely now, wouldn’t it?” He says it with a shrug of his shoulders, “So, are we doing this or not, Y/N?”

She exhales audibly before she rolls the pen between her fingers. With a last nod, she looks to him, “Alright, let’s do this, Mr. Winchester,”

  
  
  


_______________________________________________________

  
  
  


Determined, she moves to the edge, her thumb pushes the button of the pen up and down. 

“That’s my girl,” He smirks. 

And it’s not like he wanted to say it but the words slip out of his mouth before Dean can stop them. He blushes, hopes she doesn’t notice. 

She frowns, at the words but Dean acts as nothing happened. His face stays unreadable and after a while, that frown eases and she turns back around to lean over the contract. 

He watches her place her initials on every page with a shaky hand, hoping a little, that she won’t back out when she gets to the last page. 

After Y/N scribbles her signature on the last page, she exhales again before she looks over at him. 

He smiles brightly because he got his way, but also he’s surprised. 

“What?” She asks with irritation in her voice.

“I didn’t think you’d really do it,” 

“What do you mean? Please don’t make me regret this already!” The voice comes out whiny, it’s cute really. 

“It’s okay,” He moves closer to where she is and places a hand on her thigh, squeezes it for reassurance, “I promise you, you won’t regret it. I’ll make it worth your while,” 

It’s not just a phrase. He really means it. After all, she’s giving him so much of her and the least he can do is reward her for all the troubles.

To Dean’s surprise, she doesn’t push his hand away, instead, it seems like she eases to his touch. He takes that as a win. He smiles at the ease between them, “I just thought that not everyone would agree. So, really, thank you.” 

Y/N doesn’t answer. Instead, she just nods, and it seems like she is trying to avoid his eyes. Her face is flushed, though, and he can feel that her body starts to tense again beneath his one hand on her thigh.

It’s a moment later that she felt confident enough to face him again and she tucks a strand of hair back, her tongue darting out to lick at her lips, “So, uh, when do I start?” 

Dean opens his mouth to speak, but the words won’t come out because there’s the sound of the door opening. He knows who it is, doesn’t have to see the person because the only person in the whole world who would walk into his office without knocking is his own father.

Quickly, he takes his hand away from her thigh and offers it to her. She rolls the contract up and holds it tightly in one hand while she lays her other hand in his. She’s seemingly aware that it shouldn’t be laying around when it’s something only they know. Really a fucking good girl. Dean has to bite on his tongue so as not to say it out loud a second time. 

“Dean Winchester, you’ve got some explaining to do!” John shouts out loud as he makes his way into the office like he owns the goddamn place. Dean always hated that. 

He doesn’t turn around though. Instead, he still holds her hand, thumb rubbing circles on the back of it as his gaze is trained on hers. He doesn’t want to throw her right in the water and yet, here we are and the way he acts, is a reassurance that he’s right here whatever they may face now. 

His eyes are searching for something in hers, that little click, that spark, and it seems like she knows because she nods subtly. That’s all Dean needs and he leans closer to her face. His nose brushes at her temple. She smells fresh and there’s a hint of familiarity to it. Dean knows that he has made the right choice. 

Dean whispers, his voice gentle and deep, “You start right now, sweetheart,”


	4. Chapter 4

“Dean!” Mr. Winchester Sr. is still shouting and he comes to stand beside them, but Dean doesn’t even react to the imposition of his own father. 

Instead, his eyes are still on hers and he smirks reassuringly, there are little dimples showing, and from up close, his freckles are more prominent. He doesn’t let it bother him and keeps his cool. His hand is still holding hers and he draws circles on the back of it with his thumb. It feels like he wants her to not be scared. It’s calming, she can’t lie about that.

And while his father is still standing next to them, Dean’s other hand comes up to her face, knuckles brushing over her cheek. The touch makes her shiver but also it’s a signal, she knows. It’s a signal to remind her that it’s time to pretend to be his fiancée, and since his father is the main guy that they need to convince, she pulls herself together. 

Looking up at Dean, she still sees him smirking. It’s as if he wants to tell her it’s okay, and that he lets her steer the wheel. It also tells her that he’s curious about what she can come up with. 

It feels like it’s a fucking test for her.

Y/N pulls her bottom lip between her teeth as she thinks about her next move. She grins after a couple of seconds and god, she hopes he’s okay with what she’s going to do. Her one hand that’s not holding the contract goes to his tie, grabs at it and pulls him down to her.

Dean’s eyes widen for a second, but then she doesn’t know if they still are wide because she presses her lips to his and closes her eyes. 

She  _ really  _ hopes it’s okay.

He goes still, his lips slack against hers. It doesn’t hold her back from pressing closer to elicit an emotion from him. His scruff rubs against the sensitive skin around her mouth. 

_ C’mon _ , she thinks. It can’t be that hard for him, can it?  _ God _ , she’s giving it her all and he has trouble playing along? 

His lips are slack enough for her to part them with the tip of her tongue and it’s really all or nothing now because she slips it into his mouth to meet his, and it’s like something clicks in him as soon as their tongue meet, because he’s no longer just standing still.

Dean wraps his arms around her and pulls her close to his chest while his kiss gets rougher, more demanding. He molds his lips to her bruisingly hard. His one hand goes to her hair, fingers grabbing at it to pull her head back to have a better angle. He deepens the kiss, uses his teeth to bite too, making her moan into his mouth. She’s getting all hot from the kiss and the pull in her hair hurts, but it’s a good kind of hurt. One she definitely could get used to. 

They eventually have to break the kiss for air but god, she never wanted it to stop. Dean Winchester is an awfully good kisser.

There’s a loud clearing of a throat next to them, and Mr. Winchester Sr. starts to cough audibly. 

With a last soft peck to her lips, Dean draws back. He’s panting a little and his lips are slick and shiny. Her thumb goes up to brush at the wet spot and he lets her. Chuckles as she does.

“Dean? A word.” His father says with a stern voice.

Weaving an arm around her waist, he pulls her close to him as he turns to his father, “Sorry, Dad, now’s not the time. She just came back and I’ve missed her, so she’s going to have my time today.”

He didn’t particularly say it in a disrespectful way. But it sounds like he’s putting his foot down. 

Dean guides her across the room and he already opens the door.

“Dean Winchester! You come back and talk to me!” His father sounds furious and she isn’t sure if angering him is the right way to go about this. 

“I’m spending time with my fiancée, Dad. I hope you understand,” Dean lets her slip out of the room, but he stalls at the door, “I’ll call you. We can arrange dinner for you to get to know her.”

It doesn't even sound like it’s a question or something to be discussed. Dean talks like his words are final. It has some authority to it and not even his own father dares to say another word. 

He doesn’t close the door, instead, he leaves it wide open as he joins her in the hall, takes her hand, and pulls her along hastily. It’s hard to keep up and if he wants this to work, he should definitely stop walking so fast all the fucking time.

“Dean!” She hushes out a whisper.

“Huh?” He looks at her as they hurry along the hallway.

“Not so fast, I can’t keep up,” 

“Oh,” There’s a chuckle as he slows down, “Sorry,”

Now, instead of holding her hand, he lets it go to lay his arm around her waist, pushing her along rather than pulling, and it’s easier to keep up. 

When they’re in the elevator, she can see how he starts to relax. She almost pities him. 

“You really don’t get along with your father, huh?” She asks, hopes he doesn’t think she’s prying. 

Dean snorts out a tired laugh as he rests the back of his head against the elevator wall, “We don’t have the same values and standards. He’s too old fashioned,” He tilts his head to the side to look at her, “It’s fine. You shouldn’t worry about it.”

“Okay,” She lowers her head, thinking that he’ll probably be mad if she asks more. 

“You know,” Dean starts and places his hand into his pants pockets, jingles some keys in there, “We should talk about it,”

With a frown, she looks back up, “About what?”

“About the kiss,”

_ Oh. _

Her cheeks start to get warm again when she thinks about it.

After composing herself, she clears her throat, “Yeah, uh, sorry. I thought I should convince your father. If I overstepped, then I’m sorry,”

“It’s fine,”

“Was it bad? It has been a while. I don’t really know how it works anymore,” She doesn’t even know why she’s making excuses, “Next time it’s only a kiss on the cheek, okay?”

God, she tends to babble when she’s nervous and she is right now. Very much so. While she brings up all the excuses Dean started to smirk and now his lips have widened into a grin and she thinks he’s finding it all too amusing. 

“No,” He mumbles, “I was gonna say that it was good. It was probably convincing,”

“Oh good,” She smirks, “I just have to also tell you that I’m a terrible liar. I start to babble, as you can see. And my voice gets a little higher and my hands start to sweat,”

“Y/N, you’re fine,” Dean reassures her, and adds, “Right,” And there’s amusement in his tone of voice, “Just let me do the talking when you’re nervous, okay?”

“K,” She mumbles as she looks down at her shoes. 

Dean crosses his arms over his chest, “While we’re at it, is there anything else I need to know? Secrets that will blow up in my face?”

_ Ugh. _

She knew it was coming and maybe she should come clean now so he still has time to look for another fake fiancée.

“Uh,” She starts, but stops to think about  _ how  _ she can say it.

“Y/N,” The voice is stern with a clear irritation to it.

“I have a daughter,” She blurts out and exhales loudly afterward. Her heart is pounding in her chest and she squints her eyes and raises her shoulder, in fear that he’ll scream at her for not telling him about Liv sooner.

Dean doesn’t say anything, but his lips are pressed into a thin line.

“She’s six. She won’t be a problem in our arrangement as long as we keep her out of it.”

“Jesus, Y/N, you have a daughter?”

There it goes.

“Are you married? That’s a breach of the contract!” Dean gestures wildly with his hands.

“No,” She shakes her head, “I’m not married. Would I agree to pretend to be your fake fiancée if I was married? My god, I thought you could read people!” She pokes her index finger against his arm, “It’s fucking rude of you to think that, you know? Because I’m not a bad person.”

“What about the father?” 

Ugh. Again, that’s not a topic she likes to talk about, so she tries to not go into detail and only let him know what he needs to know. 

“He’s not an issue as long as we keep her out of it,”

She also wants to protect her child. Jimmy has been out of the picture for so long already, and as long as he doesn’t have to pay a fucking dime, she guesses that he won’t be a problem either. And Jimmy’s never been one who’s interested in what the rich and famous are doing. She doubts he’ll ever see a picture of her in any magazines.

Dean’s nibbling at his thumb, “The press will know about her,”

“That’s why I want you to help me keep her out of it. I don’t want you dragging her in because you want to get shares for a stupid company,”

“First of all,” He starts and holds out a finger, but he lowers it pretty quickly when he sees her cocking her eyebrows at him. He sighs as he mutters, “It’s a multi-billion dollar corporation but go on,”

“Doesn’t change the fact that I don’t want her dragged into this,”

“Right,” Dean says and leans back again, seemingly thinking about something.

  
  
  


_______________________________________________________

  
  
  
  


While Dean’s mind is still processing the news, the elevator pings their arrival and Y/N makes a swift exit. She’s probably afraid of what else he has got to say.

She has a daughter. 

That’s not something Dean was prepared for, but it’s also too late to back out now. Plus, it’s not a breach of the contract either. But Dean wouldn’t be Dean if he couldn’t adapt and roll along with everything life throws at him.

He trails behind her, watching her walk along the cars in the garage. He has to smirk because she clearly doesn’t know where she’s heading. After they have passed about four cars, Y/N stops in her track and turns around to him as she braces her hands on her hips, “I don’t even know where I’m going. What are we doing?”

Dean’s smirk subsides, but not because he’s not entertained by her but because he has to keep being the cold boss he is, “My car, we have to buy you a new wardrobe,”

Y/N looks down at herself. Her mouth opens and closes. It’s like if she wants to fight him, telling him that she doesn’t need new clothes, but she knows as well as him that hers won’t work. Not if they want people to believe that she’s his fiancée. 

He actually thinks it’s ridiculous himself because there’s nothing wrong with how she dresses, but since the press will be on her, he just wants to help so that they won’t tear her apart.

Dean takes out a key from his suit pocket, pushes at the button and a black sports car with tinted windows lights up in the distance. He first wanted to take Baby but Baby doesn’t have tinted windows. Dean doesn’t want people to see her just yet.

Opening the door to the passenger side. He lets her slip in, settles next to her right after and Dean pushes a button as the car roars to life

She keeps on watching him until he looks over and raises an eyebrow, “What is it?”

Turning to look ahead again, she shrugs, “Just thought rich people like you would have a driver, is all.”

He chuckles before he winks at her, all bravado and cockiness, “I like to be the one in control,” 

  
  
  


*

  
  


They arrive at the boutique Dean usually goes for whatever outfit he needs and as soon as they step in, the owner, Garth, is swarming over the two of them with his two employees.

Garth is not one to ask questions and Dean’s not a big talker so they forgo the awkwardness that it would bring in explaining the situation of why Dean brought a girl to buy things, Dean just acts like it’s the most normal thing, telling Garth to measure her and bring along dresses for different occasions.

Dean pulls her into a stall, and makes her wait in there while the store employee brings him dresses and clothes. He inspects them closely, thinks of where she could wear it, and what she needs to be able to pull it off as the financée of Dean Winchester.

He’s a little harsh in his judgment of clothes and dresses, but Grath knows it. Everything has to be up to his standards so he sends a lot of the dresses back before she even gets to try them on. 

Y/N tries on dress after dress and after about the seventh one, he knows that because she just said,  _ it’s the seventh fucking dresses already _ , Dean hears the groan out of the cabin.

“What’s wrong now?”

“Are my clothes so hideous that I have to get new ones?” Her voice is faint out of the changing room.

“Well, I don’t think you’re hideous. I just think you can do better,”

“Ah, great. Not hideous. A great compliment, there.”

“You know what I mean,”

“I don’t,”

Before Dean can add more to it, Garth appears with new dresses that require his attention. 

Dean chooses some dresses, one that he thinks would fit perfectly for the first meeting with his dad, and knocks at the cabin door to let her take it in and try it on, but he’s greeted with a frown.

“You know what would help immensely?”

“What?”

“If you could stop hovering in front of my fucking door. Can’t you go somewhere? Buy some clothes for yourself? I don’t know, buy the fucking store? Just go, please!”

He has to bite on his tongue so as not to laugh out loud at how cute she looks when she whines out desperately.

“Right,” Dean nods and walks out, stays close though, only around the corner, but she doesn’t have to know.

  
  
  


_______________________________________________________

  
  
  
  


By the time she reaches the last dress, the one Dean handed to her, she’s already exhausted, but she keeps on going.

Y/N takes a look at the dress, and it really is beautiful. It is the most beautiful dress she’s ever seen. It’s a little tight but still comfortable. It’s sequinned and shows a little cleavage. 

After she tries it on, she spins around, looking at herself, and smiles. It really does suit her. How did Dean know about these things? 

Deciding to show off this dress, she opens the door to the cabin and runs out, only to bump right into Dean who was standing around the corner.

“Jesus! Why are you standing here?” Her hand goes to her nose because it hurts a little from bumping into him.

“You told me to go away from there,” He has one hand casually in his pant pocket while the other one clutches at his phone.

“So, what? You just move three feet further away and that’s okay? Do you understand the concept of personal space?”

Dean slowly places his phone back into his pocket before he takes his time to look her up and down. He smirks crookedly, “Why, am I making you nervous, sweetheart?”

Y/N’s face starts to flush because yeah, he fucking does. Especially when he looks at her like  _ this _ . His eyes are dark, his gaze hungry. It’s like he’s ready to swallow her whole.

“Well,” She says, her hand goes to her hair, tucks it back before she meets his gaze, “Yeah?”

He chuckles.

“And,” She continues, “I thought I could expect a level of social etiquette. Especially with you,”

The smile’s still on his lips as he cocks an eyebrow, “In that case, I request your presence at dinner with my father tonight,”

“What?”

“Yeah, you want social etiquette, so I request it instead of demanding it as it states that I’m allowed to demand things in your contract,” He shrugs, “He just texted me, saying that he wants to get to know you. Maybe he should learn some social etiquette himself— shit,” Dean frowns and turns his head to look out of the store window.

“What?” She tries to look past him, standing on her tiptoes. 

He grits his teeth, “I saw a figure lurking outside, I think it’s a photographer,”

“Then we should give them a show, huh?” She says and it’s weird, but she doesn’t mind it that much. 

Her hand goes up to his face, tilts him around by his chin, his scruff rough against her palm. Next, she eases his frown with the tip of her fingers, smiling as she does to make him relax. 

For someone who really wants a fake fiancée, he’s really bad at faking it. 

“‘M sorry,” He mumbles, “Didn’t think they’d be here so quick,”

“Don’t worry about it,”

Y/N really means it and moves up, places a kiss on his jawline before she moves up to his cheek. Dean turns his face around and her kiss lands on the corner of his lips. He looks pained, and she doesn’t know if it’s her touch that pains him. She knows she’s not the best option, but he brought it upon himself, that’s why she doesn’t get it and it’s making her crazy that he’s so unreadable.

The glint she sees in his eyes tells her different, though. Maybe he’s attracted to her after all? At least a little? Because those eyes are darker again. Maybe he’s just shy. Which would be weird because Dean Winchester doesn’t seem like the shy type to her.

He seems to be distracted, looking back to the store window because suddenly, there are two more photographers outside. 

Her palm cups his face, turns his head so he would look at her, “Hey, Dean, look at me,”

It’s hard for him to tear his gaze from the store window, but he does, albeit reluctantly.

“Don’t worry about them, okay?” She says and smiles reassuringly.

Standing up on her toes she places a kiss on his cheek, feels him shuddering before he starts to relax to her touch. 

She knows he does because as soon as she places a kiss on his lips, Dean immediately kisses her back.

Dean wraps his arms around her and kisses her gently, his tongue only teasing at her lips, as if he’s asking for her permission. She grants it to him, opens her mouth for him to slide his tongue in. She sucks on his tongue, making him breathe out a moan and her heart starts to pump out of her chest.

Kissing a stranger should definitely not feel like this. Kissing a stranger should not leave her breathless, it shouldn’t leave her damp and tingling between her thighs. It feels like it’s the most natural thing, feels like she knows him for forever, feels like they are in sync, and it’s fucking easy.

When the shutter of the cameras die down, Dean breaks the kiss, and takes a step back, almost as if he doesn’t trust himself to be closer to her. 

He brushes his thumb over his lips, and holds it out, brushes over her lips too and there’s that pained expression again, but it quickly changes and there’s the beginning of a smirk that curls around his lips, “You know, being fake engaged to you doesn’t seem so bad,”

“Wow, you’re a real charmer,”

“Oh, you have no idea,” He chuckles, “Go change back, I wanna get out of here. You probably want to go home and relax before dinner with my father,”

Y/N nods because yeah, it probably won’t be long until this place will be swarmed by even more photographers, and god, she’d love to have time with Liv before she will be gone for a long time again. She hopes Uncle Bobby won’t think bad about the new job she took on and will be okay with looking after Liv when she’ll be gone. 

Dean talks with the owner of the store as she changes. 

As soon as she walks out in her worn-out clothes, Dean’s already waiting for her outside of the stall. He doesn’t look happy. His eyes are clouded and the exhausted Dean Winchester is back. 

“Listen,” Dean says, “Slight change of plans. You need to come live with me.”


	5. Chapter 5

Dean had made up his mind in the short span of time he told her to get changed. Had thought about the whole situation thoroughly while he waited for her to come out of the stall. He thought about the press turning up and the fact that they certainly won’t leave a single fucking stone unturned until they get what they want. 

He really did think about it. But it doesn’t matter how he twists and spins the situation around in his head, he always comes to the same conclusion. This conclusion being, that she should come to stay with him. There’s simply no other solution, even though he wanted there to be one. 

“What?” Y/N frowns at him like he knew she would and her voice comes out a shout.

He shushes her, places his index finger to his lips, which prompts her to bite on her tongue, her lips pressed into a thin line. 

Now, when everyone’s silent, Dean can hear the shutter of the camera lenses, and can see another photographer joining the ones already waiting out there out of the corner of his eye.

Wordlessly, he takes her hand and ushers her out the back. Garth knows to send the clothes to his penthouse and they have his credit card information. 

Dean opens the car door for her to slip in and like he predicted, as soon as he’s settled, she turns to him, still with those tightly pressed lips. The lips that were on his just a moment before. The lips that were so fucking soft and left him desperate for more.

Turning on the engine, Dean starts to drive towards her apartment, having seen the address on the employee file before on his computer screen. He’ll probably never forget where she lives. Frowned a little when he read it because that’s no place for a woman to live on her own, even less so for a single mom with a daughter to protect.

“What? Moving into your apartment?” Her voice is loud, carrying over the background music. He can tell that she’s irritated by his suggestion. He probably would be too. It’s not stated in the contract. She goes on, “I thought you only wanted a fake date for your social events and to meet with your dad? God, Dean, I can’t do this. I can’t move in with you, I have a daughter!”

Dean nibbles on his bottom lip as he turns into the traffic. It’s going slow, too slow for his liking. 

He risks a glance over, sees her staring out the window, seemingly trying to wrap her head around his demand. 

“Your daughter is exactly the reason why you need to come to live with me.”

She whips her head around so fast, “What?”

“Yeah,” Dean sighs and he doesn’t look at her, instead, he looks ahead, tries to find space in between all the cars, “You’ll be the center of attention as soon as the news hits the fan. Your daughter will be too, by proxy. The only way I can make sure that she’s safe from all the press is when both of you move into my penthouse. Nobody will be able to get to her there.”

“But Liv goes to school,” 

“We can get a teacher to homeschool her. At least for the length of the duration of your contract.”

“If we do, your father will know and what will he say to me already having a child?”

It’s weird how she’s still worried about his life when hers is being turned upside down.

Dean snorts out a chuckle, “My father always wanted me to settle down and have a family, guess he’ll have it sooner than he thought he would.” He shrugs, “So, what do you say? I bet the little girl likes adventures and stories of princesses and castles?”

He looks over to see Y/N staring down at her hands in her lap.

“Yeah, she does,” She says. 

“Tell her you’re going to take her to a castle. I bet she’ll love it,”

Letting out a sigh, she looks over to him now, “Well, you’re not wrong with the security, I guess. I just need to somehow tell her as gently as possible. You know,” She turns her head to look ahead, “Liv is not like other children, she needs some time to get used to new things.”

“What do you mean?” Dean frowns a little at her statement.

“Liv, Olivia, doesn’t talk to anyone except me and Bobby, my uncle,” She says, “She has difficulties adjusting to new people and trusting them. Especially men,” There’s another sigh before she goes on, “Jimmy, my ex, didn’t treat me like he should have. There was a lot of fighting and a lot of tears and Liv grew up in that toxic environment until I finally had the courage to leave. She still gets suspicious of men when she meets someone new.”

Just when Dean wants to ask why that is, she delivers him the answer right then. And it’s good, isn’t it? He should know what dark skeletons there are in her closet. However, he wasn’t prepared for that and suddenly, Dean wants to punch that Jimmy guy in the face.

“‘M sorry,” Is what Dean says. It’s probably the only thing he can say. And it makes him feel guilty for pulling her and her daughter into this. 

“It’s not your fault,” Y/N shakes her head, “I just want to protect her,”

He manages to take a left turn and the street is less crowded the closer they get to her apartment. 

“If it helps, I’m going to try to make the stay in my penthouse as comfortable as possible for your daughter,” It almost slips out of him. The name of her daughter. He almost said Liv. But again, he has no right to. He doesn’t know the child, yet, he wants to make sure that Liv will have everything her heart desires, “I will send some men who are working for me on paid vacation, if that helps. We can employ a nanny so that she’ll have someone with her at all times when you can't be there.”

“Um,”

“What?”

“If you want to hire someone anyway, would it be okay for uncle Bobby to look after Liv? It’s like,” She trails off and it’s almost as if she’s embarrassed to ask him for it, “He knows Liv and Liv trusts him. He only works in the mornings, so he usually takes care of her when she comes back from school and stays with her until I return from work.”

“Would that make you feel better?” He asks with a raised eyebrow, but to him, it sounds quite good. That way Dean doesn’t have to spend more time searching and selecting a nanny. It’s a burden he actually doesn’t need right now. 

“Yeah, it would. But I understand if it’s not okay,”

“No, it’s good. I think you should tell your uncle to come to live with you.” Dean nods his head. He’s a little worried, though, can’t lie about that. She’s a good girl and good girls aren’t treated well by the media, they never have been. But Dean would be damned if he doesn’t at least try to make it all bearable for her.

  
  
  


_______________________________________________________

  
  
  


_Was it really this easy?_

Y/N never thought it would be this easy to persuade him to agree. Honestly, she was afraid that he’d say no. She was asking for a lot, she knows, but it is really the best solution. 

Of course, Dean was right when he told her that it was more secure to live with him. She can see that too. The last thing she wants is for her child to suffer just because she made a decision that would see Liv’s life being turned upside down. 

But agreeing to do that, means that she needs to tell Bobby and even though he wants the best for her and Liv, she can already sense that Bobby won’t be that happy about it. He absolutely hates snobs and people like Dean Winchester, for that matter.

They drove in silence, the traffic increasing again. She wonders why he didn’t just let her take the metro. She’d already been home by now. 

Suddenly, a sound of ringing pierces through the deafening silence.

Dean raises his eyebrow as he looks at her, “It’s Sam Wesson, my lawyer, and a good friend. You mind if I take this?”

She frowns in reply. Mind? Why should she mind? It’s his car, after all, so she nods her head. 

He pushes the button and the ringing stops. 

_Oh._

Dean takes it via the speaker.

And she’ll be able to hear everything. That is why he asked, right?

“Sam,” Dean says as he swerves into traffic after the intersection. 

It dawns on her then, that she hadn't even told him where she lives. Dean really does know everything and is one step ahead. She figures it’s probably crucial in his position.

“Your father called my firm and demanded I tell him who your fiancée is. Apparently, it’s not Carmen?” The other man’s voice is a little raised, “Can you tell me what this is all about? Fuck, Dean, I hate to be kept out of the loop! How can I deal with your public stunts when I know jack squat?”

Dean smirks. It’s almost like he’s making fun of his friend, “Well, yeah, I am engaged. Not to Carmen. At least not anymore,”

“—Fuck,” Sam shouts out, “I’ve already had a news alert on my phone. It says Dean Winchester was seen taking a girl to buy clothes. It also says that I should stay tuned for exclusive pictures!”

Y/N watches Dean flinch at the memories. She still remembers how uneasy Dean was when the photographer turned up.

“Do I know this woman?” Sam asks, his voice still a little shrill.

“No, Sammy. She’s not known in the media and somehow I’d like for them not to find out too much about her.”

There’s a rumble of laughter on the other end of the line.

“I’m sorry, I just thought I heard you say that you didn’t want the media to find out who she is,”

“Oh, you heard me, Sam,” Dean says, his voice is deep, stern. Very authoritative. “She has signed the contract and is only available to keep up the illusion. I want her private life kept out of it and you have to help me with that.”

“Dean, that’s fucking risky. How am I supposed to pull that off? The media knows you were with Carmen. How am I going to be able to spin this?”

“I have faith in you, Sammy,” Dean nods his head, his voice comes out a low growl. 

It makes her feel things when he speaks like that. Things she shouldn’t be feeling.

Sam snorts, “Jesus, Dean! Is she even real? You sure you didn’t make her up to piss Carmen off because she has been fucking other dudes behind your back?”

Dean turns his head to her then, nods at her as a signal for her to speak. 

She nods but clears her throat, “Yeah, hello, Sam. I’m Y/N, Dean’s fake fiancé,”

“What?” Sam chuckles, “You have your phone on speaker, Dean? That never happens, what’s wrong with you?”

From the corner of her eye, she can see the blush on Dean’s face.

“I’m driving,” Dean mumbles grumpily, “Anyway, Sam, I’m in the process of moving her into my penthouse. Come meet us there in about,” Dean stalls to look at her, probably sees it on her face that she would need a little time to be able to pack up her things and move in, “Four hours. Dad’s coming over for dinner, you can join if you want.”

“And let him drive his fangs into me at the dinner table? No, thank you. But wait, what?” Sam raises his voice again, “You are moving her into your penthouse? Like, you don’t even know her, right? Dean, what the hell are you doing? No offense, Y/N,”

“None taken,” She shrugs, because yeah, she understands. She’d react like that too if she was him, probably. 

“She handled my father and the press well enough,” Dean shrugs, as if that’s the most important thing, and maybe it is.

In the background, they can hear a phone ringing. She guesses that it’s Sam’s office phone or his mobile. Depends on what phone he just called Dean from.

“Right,” Sam says, “Gotta take this, it’s Carmen. I wonder why she’s calling me,” Sam says it in a mocking tone of voice, as if he already knows the answer to it.

“Yeah,” Dean snorts out a chuckle, “I might have blocked her number.”

“Might have? You’re so funny!”

“Hey,” Dean says teasingly, “I’m hilarious!”

There’s a groan on the other end while the phone still keeps on ringing.

“Right, I see you later, Sammy,”

They have rounded up into her street and Dean cringes his nose at the sight. It’s not much, but she notices anyway. She wonders if Dean is appalled by it. He probably is. She wouldn’t live here if she had money. And soon she will have money. When this is all over, she’ll be able to move into a nice neighborhood. One where she doesn’t have to be scared to walk through alone at night on her way back from work.

_Ugh, work._

She doesn’t know what will happen after this is all over, though. Even though nothing is stated in the contract, she’s sure that she won’t be able to work for Dean’s company anymore. Even if Dean would want her to stay and work, people will talk and how weird it is to go back to working for her fake fiancé? 

But this is a worry for a later time, right? She has to get this over with first.

“Shall I wait?” He asks and it’s only then that she realizes that Dean came to a halt in front of her apartment building. She was too lost in thought to have noticed.

“No,” She shakes her head, as she grabs her bag, scrambling to get out, “If you want this, Dean, you have got to give me time. Liv is coming home in two hours, and I need to pack.”

“Right,” Dean sighs as he fishes out his business card from inside of his suit jacket. He hands it over to her and she reluctantly takes it, “Text or call me when you’re ready. Sam’s gonna be at the penthouse in four hours. It would be good if you could be there by then. If not, the dinner’s in six hours, okay?”

“Yeah,” Y/N nods, “Okay.”

  
  
  
  


*

  
  
  


She’s sitting on the couch, eagerly waiting for the two most important people in her life to arrive home. Bobby usually picks Liv up whenever it’s possible for him and he texted her a half hour ago that he’s already on his way to pick her up. 

Their belongings are packed in duffels and a worn-out suitcase and she really only packed the things she thinks she needs. She won’t be too far away and if there’s something missing, she can still come back and get it.

The only missing things now are Liv’s stuffed animals and books she’d like to take with her.

Her heart races a little faster when she hears the lock being turned.

Bobby opens the door wide, letting her daughter in first and the little girl squeals in delight and runs straight to hug Y/N, when she sees her sitting on the couch. It never happened that she’s home this early. 

The old man stalls by the door as he notices the packed bags, but he doesn’t say anything, greets her like he always does, and walks into the kitchen to unpack and clean Liv’s water bottle and lunch box.

Liv lets Y/N out of her embrace and sits down next to Y/N. It’s not that she has noticed the bags, too.

“Are you going away, Mommy?”

She leans over, kisses the top of her daughter’s head. Liv’s hair’s a little messy, just like always, “No sweetie, _we_ are going away,”

“Where?” The girl asks and there’s a little frown that Y/N eases away with her thumb.

Smiling down to her daughter she moves closer and whispers into her ear, “What do you say we go for a vacation at a castle?”

The little girl gasps, “Really?”

“Really,” She nods, still smiling. There’s a loud squeal of excitement. It almost makes Y/N’s ears hurt, “You can go pack your backpack, honey, okay? I have to go talk to Uncle Bobby.”

Liv nods enthusiastically as she runs into her room to pack the things Y/N hasn’t packed yet.

Y/N stands up as she watches her daughter go. Bobby comes out of the kitchen and sits down on the seat next to the couch and she turns to him, “You’ve heard it?”

“Yeah,” He looks sad. 

“Bobby,” She says, tries to find the words to tell him.

“You’re going away?” He interrupts her and she can tell by his voice that he’s irritated. He is pained, she knows. He loves Liv as if she’s his own and if she’d take Liv away from him, he’d be heartbroken. 

“No, Bobby,” Y/N shakes her head, “ _We_ are going away,” She says and starts to tell him about her morning.

After she finishes, Bobby nods his head but he’s still frowning, “How long?”

“If Dean’s right, it should probably take a week, two tops, but it could be longer,”

“Uh-huh,” Bobby rubs a hand over the corner of his lips as he tries to wrap his mind around it, “What if you start to like him?”

“Oh, please, Bobby,” She snorts out a chuckle, albeit a tired one, but Bobby doesn’t seem like he’s joking because he cocks his eyebrow.

“I’m just saying, Y/N,” The old man starts to say, “Liv has been your priority for so long. I don’t think you remember that you’re still young.”

“Bobby,”

“Don’t Bobby me, Y/N. He obviously saw something in you. You must have already turned his head,”

“He doesn’t even know me,”

“That will change now,” Bobby grins and god, she hasn’t seen him grinning like that for a long time. There’s some cockiness to it. Something that makes her roll her eyes to the back of her head while she groans in annoyance.

  
  
  


*

  
  


Dean had a meeting, so he sent a driver to pick her up and Bobby already started to grumble as he saw the limousine. Y/N tried to hide the amusement on her face.

The three of them are riding up the elevator to Dean’s penthouse, with little Liv’s hand squeezing her own tight. Bobby stands with his back pressed against the elevator wall, muttering something to himself and she just knows that he absolutely hates elevators. It’s also not helping that the ride is such a long one to get to the top of the building.

Right when the three of them step out of the elevator, there’s already a tall man waiting in front of the door to Dean’s penthouse. The man’s hair is a little longer, and he wears a sweater with elbow patches over his shirt.

“Hello Y/N,” He says, “I’m Sam,”

“Oh, hi Sam,” She greets him back and Sam extends his hand for her to take. He goes on to greet Bobby and gets down on his knee to say hello to Liv. 

She likes that. Likes it when people are considerate and try to accommodate her child. Not enough people do that and it literally warms her heart that Sam makes the effort. She wonders if he has kids himself, but probably not. Successful men don’t really need children to stand in their way, do they?

“You must be Olivia,” Sam smiles, it’s quite sweet how he acts, but Liv’s hiding behind her body and buries her face against the side of her. It makes Sam chuckle, “You wanna see your room, huh?” He gets back up then, standing up straight and towers over all of them. He’s a couple of inches taller than Dean and when she first saw Dean, she already thought that he was super tall. “Welcome to the penthouse of the icy King,” 

Sam opens the door and there’s a grin on his face. She is taken aback a little, because that nickname is only circulating around in the company, she had no idea Sam would know about it.

He winks at her in passing, whispering, “Who do you think spread the rumor at the company in the first place?”

Her eyes widen but so does her grin, “Oh, you didn’t,”

“Sure did,” Sam nods his head and shrugs, “He pissed me off at golf, so,”

She’s still chuckling when Sam follows them into the hallway. He quickly makes his way to the front and they take a sharp left turn at the door and down a long hallway.

“These are guest rooms,” He announces, “Dean’s room is through the living room, so this wing is solemnly yours to use. He thought it would be better if you have your own empire in the castle,” Sam looks down to Liv and winks at her. The girl smirks, but that’s about it. “You can come and go as you please without having to go through the whole apartment, plus you have your own little living room and a kitchenette for when you feel like you want to cook for yourself. But you are free to use the main kitchen, living room and gym. The fridge here and in the main kitchen is always full and if you ask nicely, the chef and maids will be delighted to whip something up for you should you don’t feel like cooking. There’s a pool on the terrace too, if you want to take a swim.”

Wow, it sounds like a castle indeed.

“Is Dean home yet?” She asks, wondering why Sam’s showing them the apartment and not Dean. Maybe Dean doesn’t want anything to do with them more than he has to, which would be totally valid and she’d understand.

“I haven’t seen him yet,” Sam says as he stops in front of a room, “I know he went out to buy things for your stay and told me to be here when they will get delivered. He’s rushed back to a meeting though, but he should be here soon,”

“‘K,” Y/N nods. She didn’t even know why she asked. Not that it matters. At least it shouldn’t.

“So, Olivia,” Sam changes the subject, “Are you ready to see your room, huh?”

Liv’s expression stays cold, but she nods her head.

“Let’s check it out, Olivia,” Sam opens the door to Liv’s new room and lets the little girl go in first. Liv’s still clutching at her hand so she automatically pulls Y/N with her. 

“Wow,” She says and watches as Liv slowly lets go of her hand to walk further into her new princess themed room. It’s a stark contrast from home where there’s only a single bed with a bookshelf for her books and some stuffed animals.

There’s a wooden castle in white and pink standing in the corner. It’s big enough for her and Liv to sit inside. A white rocking horse stands nearby. In the other corner there’s a little table with a porcelain tea set, ready to be used for tea parties. A giant stuffed teddy bear and a dressing mirror with tiaras and feather boas stand in the middle of the room. God, this room is what princess dreams are made of. 

Dean did this? She’s sure he did because Sam said he went out to go some shopping. He really didn’t have to, but he went out of his way to organize a room she’s sure Liv will like to stay in and that counts as something in her books. 

Eagerly, Liv goes into the castle, smiles and waves out the window of it. 

“Do you want to wait here while I show your mom her room?” Sam asks her child. 

She absolutely loves how he always involves her daughter. Liv nods and she already skips to the other side of the room to sit at her little table, fingers touching the porcelain. Y/N hopes it’s not expensive porcelains because children can be clumsy, especially Liv.

“This way,” Sam makes his way out and just next door to Liv’s room, he opens the door to her room, “Dean thinks you want to be close to your daughter. Bobby’s room is right next to your living room.”

“I’ll find my way there on my own,” Bobby says and they both watch him go. 

Sam just shrugs, but she guesses he knows how old men are who aren’t used to this kind of lifestyle. She’ll check up on him later but she’s curious about her room. 

When the tall man opens up the door for her, she’s speechless. There’s a big bed, bigger than the one she has at home and a floor to ceiling window that overlooks the city. 

Off to the side is a huge closet, the doors of it open. Dresses she was trying on today spills out of it in all different colors. There’s a bathroom to her right too. She’s never had an en-suite in her life. 

“Wow,” She chokes out, still a little taken aback by the generosity of the apartment and Dean. 

Before Y/N can say more, a woman appears behind Sam. 

“Finally,” The brown haired woman says, but it’s with a big wide grin.

“Y/N, this is Pamela, your stylist,” Sam introduces them and Pamela pulls her into a hug. 

“Um, I don’t need a stylist,” 

“Sure you don’t,” Pamela rubs along Y/N’s arms, “You’re actually quite pretty, we’re just going to make you look a little bit more like Dean Winchester’s fiancée.”

Looking over to Sam, Y/N sees the man shrugging, “Right, I’ll be in Dean’s study. Come see us when you’re done.”

With that, Pamela closes the door and prevents her from escaping.


	6. Chapter 6

It feels like she’s been sitting down for ages and she’s worried about Bobby and Liv. Sure enough, Sam sensed her worries and texted her that they are both being taken care of. So at least there’s that. 

Pamela made her slip into the sequin dress after her shower and the woman put some makeup on her face.

“Not too much, okay?” Y/N says, just making sure because she still wants to be herself after all.

The brown haired woman chuckles, “Don’t worry, babe, I’ll just turn up the volume a little, you’re fine the way you are. You have a cute face, don’t want to hide that below too much make up anyway,”

With careful strokes, Pamela shows her how she can apply it herself for her next outings and yeah, Y/N can’t say that she doesn’t like that. Because it seems hideous to always have a stylist at hand, no? She didn’t sign up for this crap.

When Pamela is done, she leaves with a contented smile on her face and Y/N walks over to the floor lengths mirror that’s attached to her closet to catch her own reflection. She wears heels, has to still get used to it because they are way higher than the ones she wears for work. Apparently being fake engaged to Dean Winchester comes with a sacrifice of her feet. 

Her eyes trail up her body from her shoes to her face and it’s weird because she thought that she’d probably not be able to recognize the women who will be staring back at her, but she does. Pamela was true to her word, she just really turned up the volume to Y/N’s boring self. 

Okay, now is the time to present herself, she guesses. Sam had said that they’re waiting in the study. She’s yet to find out where it is, though. 

Sticking her tongue out at her own reflection, she starts to chuckle. She’s living the life she never thought she’d get to experience and god, she hopes she won’t lose herself in it.

With a last look around her new room, she makes her way to Dean’s study.

  
  
  


_______________________________________________________

  
  
  


Dean makes his way into his study after having rushed home after the meeting to take a shower. He had been sweating bullets since this morning and it was refreshing to say the least. It would have been better if his dick wasn’t half hard when he thought about Y/N. He didn’t rub himself off, didn’t let himself go there and jerk off to the image of a girl he paid to pretend to be his fake fiancée. He was afraid that it would uncover things he didn’t need in his life right now. 

So, when he pushes the door to his study open, his dick is still semi but Dean thinks it’ll go away soon. Especially when he thinks about the dinner with his dad because that meeting is what nightmares are made of.

Sam’s already waiting on the couch, nursing a drink. He probably had a rough day as well and Dean can’t blame him. He walks over to his mini bar, pours himself two fingers of whisky and sits down with a grunt across from Sam.

“Go on,” Dean says, “I know you have a lot to say,”

The other man just chuckles, “She’s cute and pretty, you didn’t mention that,”

“Is she?” Dean cocks an eyebrow and takes a sip from his drink, “You’re right, I didn’t.”

“You like her, don’t you?”

“Sam,” Dean snorts out the man’s name, “I don’t even know her. She was in the right place at the right time,”

“You were never a good liar. I could always see through you.”

Dean frowns, “What do you mean?”

The other man chuckles as he takes a sip and lets the liquid travel down his throat, “You could have chosen anyone for that. The execs in your meetings, the ones working just below you, yet, you picked her.”

“Are you trying to go anywhere with this?” Dean asks with clear irritation in his voice. 

“Wait for it,” Sam says before he takes another gulp of the brown liquid in his glass and Dean rolls his eyes. Sam grins before he goes on, “All our lives, you have never  _ picked  _ a girl, Dean. Mostly they offer themselves to you, even back at school, do you remember?”

Oh, yeah, he does remember. Sam’s not wrong, but still.

“They offer and present themselves to you or your father picks them for you to bring along to social events and most of the time, you’re a one date kinda guy. You never ever picked one on your own.”

“You say it like women are something you find in a field,”

“Am I wrong?” Sam raises an eyebrow to match Dean’s, “Fact is, you picked out Y/N, even though you could have waited. You could have talked things through with me, wait until Carmen gets back and we could have come up with a plan. You know that she isn’t in for you either, she’s signed a contract and was willing to sign that prenup.”

“I didn’t want to wait for Carmen to come back to me,” Dean’s voice is stern. He really didn’t, he didn’t want people to think he let it slide when she’s been cheating on him. How will it make him look? He’s not a fucking idiot.

“I’m just saying that you’re being hot headed doesn’t help us at all. And the fact is still there that you’ve picked her and that means something in my book,”

“What stupid books are you reading?”

Sam chuckles and ignores Dean’s remark, “Carmen boarded the next plane back, by the way,”

Dean takes a sip from his drink, thinks about Sam’s words, “You can tell her that she doesn’t need to show up. I’m not taking her back when I have Y/N,”

The other man’s grinning from ear to ear and Dean rolls his eyes a second time, “And no, I don’t really like her. I barely know her. I just find her interesting, is all. She’s different to all the women I’ve ever met.”

There’s a laugh coming out of Sam and Dean scoffs annoyingly. 

Just when Dean wants to open his mouth to tell Sam to shut the fuck up, there’s a knock at the door. 

They both turn their heads to see Y/N open the door to his study. Dean feels a rush of blood to his head. How long has she been standing outside? How much did she hear? But before he can think about being more embarrassed, another punch knocks him out when he sees her walking in with her beautiful dress. 

“Sorry,” She says, “Am I interrupting?”

Dean has to clear his throat before he’s able to speak, “No, you didn’t. Come in,”

She nods and walks further into the room. She looks absolutely stunning, a really stark contrast to the look when he met her. It’s not that she was ugly before, she wasn’t — isn’t. He can see that she only wears minimal makeup.

“How do I look?” She asks with a smile as she twists around in her dress and somehow Dean wishes that Sam wasn’t here to see her like this.

“You do clean up nicely,” It slips out of Dean. 

Clean up nicely? What the fuck did he just say? Who says that?

“You look beautiful, Y/N,” Sam chimes in to probably play off the stupidity that Dean just let slip out of his mouth and Dean sends him a grim look. 

But it doesn’t stop there because Sam ignores Dean’s look to wink at her. He’s a little irritated by it, to say the least. 

“So, Y/N,” Sam says, “Do you care to tell me how you two met?”

“Sam, aren’t you late for your appointment?” Dean interrupts.

Sam looks at him puzzled and it takes another two seconds until he catches on, “Oh, yeah. It was a pleasure to meet you, Y/N. I’m looking forward to working with you because you’re a delight,”

The tall man stands up and takes Y/N’s hand, places a kiss on the back of it before he leaves and Dean tries his best not to let the feeling of jealousy hit him. He doesn’t know why he should feel jealous anyway. There’s nothing to be jealous about. It’s a business deal. He should be used to it, right? Right.

“My father will arrive in thirty minutes,” Dean says drily, his throat restricting the longer she looks at him. 

“Is there anything I need to know before you feed me to him?”

Dean lets out a small snort, “I’m not  _ feeding _ you to him. I’m there too and can help out. When I think of it, maybe it’ll be good if we could establish the story of how we met.”

“Oh, I know!” Y/N shrieks out and gets all excited. Dean thinks it’s really cute. “How about I got into the elevators so quick which made you spill the coffee you’re holding over your shoes and pants? Like, the story is really partially true and it would be less hard for me to make it sound trustworthy,”

“Go on,” Dean nods his head, and empties his glass before he sets it down on the table before him. 

Her long legs and the away she sits doesn’t help his state of mind. The dress has ridden up on the couch and Dean tries to look anywhere other than at that exposed flesh that he’d like to sink his teeth into.

“I was afraid that you’d be mad at me so I offered to buy you a coffee to make up for it, but you didn’t want that because you were late to a meeting. But I was persistent and waited in front of the door and asked you so many times if you wanted a coffee and to please let me make up for ruining your suit. And somehow you agreed, maybe just to shut me up. We went on a coffee date every day until we fell in love.”

After her story, she smiled satisfactorily. The smile of a winner if he ever did see one. One he shows too often after a done deal. 

“I don’t really have time for coffee dates,” Dean adds his two cents, knowing that it doesn’t sound quite nice but he just can’t help himself. That’s the way he is. The way people expect him to be.

There’s a little pout on her lips, and Dean’s not prepared for that because it looks too cute, “I mean do you have a better idea?”

“No,” Dean shakes his head, “I like it, I never said I didn’t,”

“Good, but I’ll let you come up with your proposal story, okay? I feel like I can’t pick my brain anymore than I already have. It has been a long day.”

“Right,” He stands up and pats his thighs, buttons up his suit jacket too because he thinks it hides his more than semi hard dick pretty well, “Wait here, I’ll be right back,”

  
  
  


_______________________________________________________

  
  
  
  


Dean leaves the door open and Y/N can hear his heels clicking on the stone flooring until the sound is out of earshot. She wonders what he’s up to, feels a little nervous about it.

While Dean’s gone, she gets up from the couch and looks around the room. The study is spacious, like every room in this ridiculously big penthouse, she guesses. There’s a desk at the far wall, a bookshelf graces the other wall. It’s full of books. She wonders if Dean really reads. It doesn’t seem like he has the time to do so. She wonders if he relaxes at all because he seems so tense all the time. Maybe he only tenses up when he’s around her, at least she can’t help to feel this way.

There’s the group of sofas where she was sitting on but right by the floor to ceiling window is another sofa that looks out over the city. She wonders why that is because the sofa seems a bit out of place. 

Standing by the window, she’s looking out over the city, the people and cars seem so small from up here. She doesn’t dare to touch the glass though in fear that she’d leave handprints all over it. Dean probably won’t be happy about that.

She’s lost in thought, wondering over and over again if she had made the right choice. It was a spur of the moment thing. She does a lot of those, like the time she hooked up with Jimmy for the first time. They were at a frat party and she knew him from her communications class. She let him drive her home, even though he was definitely not fit enough to drive but her head was spinning and she might have had a couple of drags of a joint too many. They didn’t even make it into her apartment, fucked right in the backseat, not worrying about contraception. 

By the time she knew she was pregnant, it was too late to abort, and honestly, she wouldn’t know if she would have. It’s not the baby’s fault. She and Jimmy tried to make it work, even though he was always suspicious if the baby was really his. Jimmy’s parents were loaded and he had a bigger apartment close to campus, funded by his parents. She moved in there because his parents wanted it that way, not because he did. While Jimmy was still enrolled and finished his degree, she dropped out to care for their baby. He eventually graduated but stayed in college to pursue his Master's degree. 

When Liv was four, Y/N wanted to try her chance at the job market as well, but Jimmy was against it. His parents were too, apparently, because they said that she wouldn’t be able to give their grandchild a good future and they wouldn’t stand to have their name dragged into this. She fought tooth and nail to keep Liv and changed the child's name back to her own. And after a long fight, they eventually agreed that she would take Liv, and Jimmy was not to pay a single dime. 

Getting out of the abusive and loveless relationship was probably the best decision of her life up until that point. Jimmy drank a lot and was overall not happy. He would lash out at her and she didn’t know why she stayed. Maybe there was a shred of hope that she desperately tried to cling on to. 

So, when she moved out, she stayed with Bobby for a while until she found the job in Dean’s company, and then it went pretty quick. She and Olivia moved into their own apartment.

A year later, she heard the news that Jimmy’s parents went bankrupt and Jimmy was trying to hold himself above water after he developed a drinking problem. Apparently, Karma’s right there helping her. 

She’s so deep in her thoughts that she doesn’t notice Dean returning, only realizes it when a figure is standing behind her. Startled, she jumps a little as she turns around. 

“Sorry, didn’t mean to scare you,” He mumbles as he steps closer to the window to stand next to her and they look out of the window together. It’s romantic, she thinks, with the backdrop of the city, especially at night.

Looking over to Dean again, she notices him holding a velvet box in his hand and smirks, “Is that a ring, loverboy?” 

Dean sends her a look accompanied by a little frown. Something that says, _ I have heard it but I won’t say anything because it’s stupid _ . Well, he might not be wrong.

“Sorry,” She breathes out, “I told you I tend to babble when I’m nervous,”

He sighs and lifts his eyebrow before he opens up the box and it is as if the air has been punched out of her lungs. 

“Wow,”

The ring is absolutely beautiful.

Dean smirks and clears his throat before he speaks, “It used to be my mother’s,”

It wasn’t like all the engagement rings Y/N’s seen that the rich and famous women are wearing nowadays. This one is modest, might even be boring and too normal compared to those. The ring has a bigger round diamond in the middle, with two smaller accompanying stones on its side. It’s a gold color ring too, not white gold like they usually are. It looks special and it looks like it has more sentimental value around it than monetary value. Maybe that’s also why she thinks it’s so precious.

“Dean, I can’t possibly wear this ring,” She says, but his hand already goes to her left one, grabbing it and holding it up to slip the ring on her finger.

He pauses to look at the ring, smiles as he sees how it fits. How did it fit anyway? How is that even possible? 

“I was right with the measurement,” Dean chuckles and she thinks that he wants to turn away, but he’s still standing here holding her hand, “I want you to wear it whenever you’re with me, okay?”

She can not do anything else but nod.

“I proposed to you on this rooftop, overlooking the city,” He says and it takes her a while to realize that he’s talking about his proposal story that he’s suggesting.

“Right,” She bites her lips and looks down to the ring briefly before she looks up to meet his eyes again. They are glistening a little, and there’s a hint of a smirk on his face. Right here by the window, his freckles are prominent on his face. 

Y/N’s distracted, feels the urge to count them.

“We were alone and we just had a meal. It was a warm summer night and we took our desserts on the terrace,”

She can picture it clearly and her heart starts to beat faster. 

“I didn’t prepare a speech,” Dean clears his throat, and adds, “And the things I said weren’t particularly romantic,”

“It didn’t matter, because I know that you feel more comfortable showing your actions rather than using your words,” She chimes in, “There’s no romance needed, no sappy words, because you already show me enough how much you love me,”

There’s a sparkle in his eyes after she said it. Somehow she thinks it’s fondness, but then something changes and he avoids her eyes. Instead, he looks down to the hand that’s still holding hers. His cheeks are tinted pink. It’s totally cute how embarrassed he gets. 

“So,” Dean swallows, “The contract says that we don’t touch each other more than necessary, especially not in private. But since my dad will be here, we will probably need to keep up the illusion, don’t you think?”

“Dean, the only one who seems to be uneasy and flinches at my touches is you,”

The pink in his cheeks rises up to his ears, “Yeah, I’ll try to change, okay?”

“I want you to feel comfortable. And please know that you touching me doesn’t bother me. I’m not disgusted or disturbed by it, okay?”

He nods, “I’m not—” He starts, but stops to exhale, and then he tries again, “I’m not disgusted by your touches, I just need to relax, I guess,”

“What would help you relax?” She asks and she means it. Maybe she can help. 

“It would help if I knew that I didn’t pay you,” He chuckles drily, “Dad will be here soon so let’s get this over with,” He pulls her along to the door and her grip tightens around his hand. 

She’s so fucking nervous.

“What if he hates me?” She whispers just before they reach the door and Dean turns around, places a hand where her shoulder meets her neck.

“My father wouldn’t like you even if it was real. He has high standards,”

“That’s fucking reassuring, thanks,” 

Dean chuckles, “It doesn’t matter what he thinks, okay?” He rubs along her arm with his other hand, “Can you pretend to love me for a while, Y/N?” 

“It depends,” She says with a shrug and his eyes widen. She smirks then to ease the situation because he obviously doesn’t get the joke. “Can you pretend that I’m the only thing that keeps you going? Pretend that I’m your first thought when you wake up and the last before you fall asleep, Dean? It’s more challenging for you with the array of women you’ve dated,”

He smiles crookedly, and there’s that glint in his eyes again, “Oh, sweetheart, I’m not worried about my end of the bargain,”

Her face feels hot all of a sudden but she frowns after she catches herself, “Of course you’re not because you have nothing to lose,”

The frown on Dean’s face matches hers from before, “What are you talking about?”

“Yeah well, if I screw this up, I will lose my job and a steady income but you?” She pokes at his chest with her index finger, “You, Mister, will probably get a lecture from your dad, but you’ll be back to dating super rich women and beautiful models, and you can go on with your life as if nothing happened.”

Dean chuckles and he looks kind of amused? Which is not fair at all when she’s all worked up.

He pushes both his hands into his pants pockets, balances back and forth on his heels before he leans down to be on her level, brings down the air with him and she can smell his cologne. It’s intoxicating. 

“Tell you what,” Dean smirks, “If this blows up because of me, if they should see through me or if anyone should question my feelings for you, I’ll buy you an apartment and I’ll help you secure a job. I have connections. Somewhere where no one knows that you were being engaged to me. But,” He darts his tongue out, licks over his lips and she bites down on her own because she knows exactly how they feel, “If you make a mistake and it blows up because of you, sweetheart,” He makes a pause and stands back straight.

“I have nothing you’d want,” She shakes her head.

“There’s something,” He shrugs and he says it so easily too. She can’t help but frown in confusion.

“What?”

“If it blows up because of you, Y/N. If you fail to convince the world how much you love me,” He grins, and the grin grows cocky, “You’ll marry me,”


	7. Chapter 7

Y/N’s mouth opens and closes in quick succession.

She keeps on shaking her head, “I’m sorry, I think I must have not heard right,” She starts to chuckle but it’s not a good chuckle, it comes out more drily, like she tries to override her confusion with it, and Dean cocks an eyebrow, thinks she’s adorable how she keeps shaking her head. “I thought you said that if this should blow up because of me that I’d have to marry you,”

“That’s exactly what I said,” His voice is steady because he really means it.

“Oh no,” She shakes her head again, continues to look at him puzzled, “You can’t be serious,”

“I’m dead serious,”

“Dean, you don’t even know what you’re saying,” She looks around the hallway, looks up at the ceiling, as if she’s trying to spot a damn camera. 

“Hey, Y/N, look at me,” Dean waits until her gaze is back on him and then he stares her down, “Sweetheart, do I look like I’m joking?”

She narrows her eyes as she looks at him, and Dean notices that she tries to see in his eyes if he’s joking. He can tell that she’s trying to read  _ something _ . Fucking anything. But she can’t. They never can. Maybe she’ll get it, she never will. He’s hard to read, is not really an open book. He doesn’t think there’s anyone out there in this world who can read him and that’s because Dean wants it that way. He has built up his business persona, has shaped himself to be unreadable, unpredictable even. It works to his advantage.

Her eyes go back to their usual size, but there’s a frown between her eyebrows, “Give me one good reason why you would want that?” 

Dean reaches out his hand, grazes her cheek with his knuckles before he moves his thumb up, rubs gently in between her eyebrows with it to ease the frown. 

“I think,” He starts to say and pauses to clear his throat, using the time to think his words thoroughly. His thumb leaves her again, pulls his hand back and sticks it back into his pants pockets. He only realizes it now that he’s been touching her. Has been touching her more than he probably should. In private. After he composes himself, he starts to speak again, “The most important reason is, that eventually, I will have to get married anyway. I should keep up our arrangement, it just seems easier.”

It’s not bad for him, who’s a businessman, to want to stick to a deal that’s already going on when both parties benefit from it, right? Right. But somehow there’s a feeling in his gut that tells him that what he just said was wrong.

The frowns back and she looks at him like she doubts him and there’s something he can detect in her eyes that he can’t quite put his finger on. Was it disappointment? 

He quickly tries to save the mood. 

“But don’t worry,” Dean chuckles and looks down at her, pulling his chin to his chest. It’s most definitely not his best angle, most definitely he doesn’t look like the hottest entrepreneur 2020 like this. But hey, she’s stuck with him now and he’s stuck with her. Time to get accustomed to the side that’s not always rainbows and cupcakes, and somehow it works because the frown’s gone. “It’ll only happen if you lose,” 

Y/N snorts. She’s trying her best to keep her cool he guesses, and she crosses her arms over her chest. It prompts her tits to be squished and they almost spill out of because of the wide cleavage. Dean knows he shouldn’t but it’s almost impossible. So, he does what every man would be doing, he risks a glance, hopes she doesn’t notice. 

But she does. Because he knows by the way the corner of her lips curve up that she must have noticed him staring. And it’s like she’s taunting him because she presses her arms together some more as she starts to grin. It’s all cocky and fuck, he’d never thought he’d see a cocky smile on a girl that matches his. 

“Fine, just don’t come crying when you have to fork over a new apartment, loverboy,” She ends up smiling satisfactorily, it’s almost too cute.

Dean chuckles again, “That only happens when I lose, sweetheart,” And then he leans closer, brushes his lips against the shell of her ear to whisper to her. It could be his imagination, but she’s shivering. From up close he can smell her perfume, and he absolutely loves the scent on her. Dean keeps his voice low when he speaks, “And I never lose, baby,”

Standing back, Dean holds out a hand out for her to shake. Y/N does, with a narrowing of her eyes, grips his hand just a little tighter to tell him silently, that’s she’s not a loser as well. 

He likes that. Likes how she absolutely is down to compete. 

“Got yourself a deal there,” Dean nods and instead of letting go of her hand, he holds it tighter, keeps it in his as he pulls her along the hallway and into the dining room.

  
  


*

  
  
As he pulls a chair out for her to sit on, the doorbell rings. Dean should have known, his dad’s never late.

“Dean,” She whispers.

“What?”

“Why is there so much silverware?”

He laughs. Full on.

She elbows him in the ribs because the footsteps of his father and the maid are coming closer. 

“Seriously, which ones do I choose?” Y/N hisses.

His father is already in the room and comes closer, so Dean leans over to her, whispers into her ear, “Work your way from the outside in. They are placed in the order of use. It’s not hard,” 

“‘K,” 

She nods, but the frowns still there so Dean reaches under the table, lays his hand on her thigh, squeezes reassuringly and she wants to stand up and greet his dad, but Dean holds her down, thumb drawing circles on her skin, “Stay,”

They aren’t formal. His father usually sits down to eat because that’s what he came here for. It’s not a fucking social party. There are no eyes on them and John Winchester doesn’t go out of his way to impress anyone when the press is not around.

And as Dean predicted, his father sits down before he even greets them.

“Y/N, Dean,” There’s a courtesy nod.

  
  
  


_______________________________________________________

  
  
  
  


Dean and his dad hold small talk and it isn’t two minutes later that the maid brings in their first course. 

While she was getting dressed, the chef sent the maid around to ask her if there’s something she doesn’t like or if there’s something she is allergic to and Y/N guesses that they are pretty happy that she could literally eat anything. She grew up not having too much food around so food in general gets her excited and she loves to try new things.

When the maid sets their entrees in front of them, Dean’s hand leaves her thigh, and she doesn't even notice that he’s been touching her the whole time. Is it weird that it felt natural to her? Somehow, she has the feeling that it doesn’t seem that he noticed it either because Dean just pulls his hand from her thigh and starts to dig into his food like it’s no big deal.

Maybe it isn’t. Maybe, she thinks, he really enjoys touching her to feel close to her and that’s a good start, right? At least he doesn’t look as troubled as he usually is around her.

It’s chicken truffles terrine on a salad bouquet and god, the terrine melts on her tongue and there’s an explosion of tastes going on in her mouth. 

She hums her approval after the first bite, which prompts Mr. Winchester Sr. to smirk at her. 

The conversation is kept light during the first course, maybe Dean nor his father wanting to spoil their appetite. And she keeps herself mum, too afraid she would start to bubble nonsense because she’s still so damn nervous.

“Sauntéed Dover with Almond and Soy-Lime emulsion,” The maid said as she brought out the main course and honestly, Y/N doesn’t understand any of it but hell, if it’s as good as the entrée, they should keep bridging them out.

Before she could dig her fork into the glorious fish, though, John Winchester clears his throat to speak. 

“So, Y/N, I heard you are working in our company?”

Her heart starts to race and there’s that sweaty hand again. 

She pulls herself together and looks at Mr. Winchester Sr. tries to meet his eyes because she doesn’t want to seem like she’s incapable of answering a damn simple question. 

“Sir, yes. In fact, I met Dean there,”

The fact that she held his eye contact works, because John nods, before he takes the fork and digs into his meal. The relief she feels when John doesn’t ask more questions is vast. 

She takes a bite of the fish herself and it falls apart as soon as the fork touches it. Her mouth starts to water before she pushes the forkful of fish into her mouth and she isn’t disappointed because god, that explosion of taste is back and the fish melts on her tongue. 

Humming out loud, she closes her eyes, savoring the fish and the taste of the soy-lime sauce. 

Dean chuckles next to her when he hears it, and his hand is back on her thigh, squeezing it in what she hopes is approval. 

When she opens her eyes, she sees John watching them, but there’s a smirk on the older man’s lips. 

“It’s good to see a woman with an appetite,” He says.

“I’m sorry,” Her face feels flush, “I just get very excited about good food,”

Dean’s hand squeezes her thigh again, as if he wants to say that it’s okay. 

His father is watching them, though. She realizes as she looks back to the old man and he still hasn’t budged. That’s when she knows that he’s watching if they are real. 

Y/N leans closer to Dean, lets her hand trail up his muscled back, her fingers threading through the short hair at the nape of his neck and the color in Dean’s cheek rises up. His ears are tinted pink. She clearly affects him. She just doesn’t know if it’s good or bad. 

Before she can move closer, Dean almost winds himself out of her grip, and his hand that’s on her thigh goes behind him, plukes her hand away from his neck to hold it in his palm. 

“Are you okay?” She whispers, doesn’t want to be too loud, even though his father has seen everything already. Clearly, he’s not okay, but she just doesn’t know what it is. Does her touching him hurt him so much? Why do they keep doing it then? 

Dean catches himself, places a kiss on the back of her hand before he moves closer to kiss her cheek. He stops short, to whisper in her ear, “No, I think I’m in trouble,”

His lips lingering close to her ear, sending shivers down her spine. What does he mean he’s in trouble? How? What? 

Before she can wrap her head around what Dean just said, John clears his throat to speak.

“Y/N, what do you think about my son’s prenup?”

If John thinks he caught her by surprise, he really did. 

“Uh,” She starts to say, stammers as her mouth tries to form words. Of course, Dean Winchester would have a prenup. Sam mentioned that Carmen was ready to sign that thing. It’s not a secret that wealthy men have prenups, right? 

“He hadn’t shown you the prenup yet, did he?” John’s lips are crooked into a cocky grin. 

And it’s then that Dean turns to her and lays his hand back on her thigh, “I didn’t show it to you because we won’t have a prenup,” His voice is soft, gentle while his eyes are on her, as if he wants to make sure that she hears him. 

“You what?” Mr. Winchester Sr. asks loudly.

Dean’s eyes leave hers as he tilts his head back to meet his dad’s gaze. “I won’t have a prenup with her, Dad,” His voice is louder this time, firm, as if he is putting his foot down.

“Dean, I—,”

“—No, I know exactly what you want to say. Fact is, it’s my marriage, and my life. You have no say in this. I trust Y/N. We don’t need it and that’s my final word.” He’s even louder, getting all worked up and it’s her turn to lay her hand on his thigh to calm him down. 

He flinches at her touch, just a little, but she notices it nonetheless. And she gets a bit discouraged. Why does he bother holding a speech with not getting a prenup when he flinches at her touches? She doesn’t fucking get it.

John Winchester stands up abruptly and buttons up his suit jacket, “Well, it was nice, but I have another dinner meeting to attend,” He says as he nods to Dean and her, “Dean, I’ll see you at the event, and Y/N, it was nice meeting the woman who manages to enchant my son enough for him not being able to think straight.”

The man walks over to the door, stalls and looks back, “I will get Sam to talk some sense into you, and I hope next time I see you, you’ll have changed your mind.” He says, completely ignoring her presence.

“Wow,” She huffs out as soon as the apartment door shuts close. 

“Yeah,” Dean snorts, “That’s my father for you.”

She wonders if she should bring up the prenup, but decides against it. It’s not like they’re going to get married anyway, right? Surely, Dean’s legal team will be able to find a solution before they have to go that far and she certainly will not lose the bet they have running.

Returning to her meal, she forks the fish into her mouth, groans loudly this time because the old grumpy Mr. Winchester is gone and Dean sets his fork to the side and braces his elbow on the table. He turns his body a little, tilts his head and lays it on the hand of the arm that’s on the table as he continues to watch her eat with a grin on his face.

“You really like the fish, huh?”

“God,” She exclaims, “The food here is excellent,” 

“I’ll pass your compliment to the chef,” 

“I hope me gaining weight is not in the contract because I think there’s a big chance it will happen if I get fed delicious meals,” Y/N smiles at him with her mouth around the fork. 

“It isn’t,” Dean replies and it seems like he really enjoys her enthusiasm.

He hasn’t touched his food, but he’s waiting patiently for her to finish hers. As soon as she does, he gets up and holds out a hand for her to take, “C’mon, we’re taking the dessert in my study.”

“In your study?” 

“Yeah,” Dean grins as he leads her out, “I would have suggested having taken it on the terrace, but it’s too chilly and you’re barely wearing anything. The next best view in this penthouse is from the study window.”

He leads her inside and he’s not really wrong. Now that it’s dark out, the city below them is lit up by a million lights. 

“Is that why it’s your study? Because you spend your nights here often and you wanted a good view?”

Dean hasn’t turned on the light in the room, but there’s enough light coming in from the window that she can see his cheek turning pink, “Maybe,” He shrugs.

Thinking that it’s probably something he doesn’t want to talk about, she makes her way to the couch right by the window, takes off her shoes and curls her legs on the sofa. 

The maid comes in to bring them the dessert and a refill of her wine glass. It’s a really good wine, she can’t lie. It makes her feel woozy in the best kind of way and she can’t stop wanting more, even if her head’s already swimming a little. 

Y/N looks back to see Dean pouring himself a couple of fingers of whiskey before he takes off his suit jacket. He didn’t bother wearing a tie to the dinner. He opens up another button, and it makes him look more relaxed. He sets his glass on to the tray and balances the items over to set it down on the little table next to the couch.

He hands her the plate with what she assumes is something chocolatey. 

Digging her silver spoon into it, she takes a bite, hums and groans as the flavor hits her taste buds. It’s dark chocolate, which normally she doesn’t really like that much, but it’s spiked with something she can’t put her finger on but it’s fucking delicious. 

“Oh my god,” She moans, “It’s so good,”

“I can tell,” He chuckles as he watches her eat.

“Wait,” She pauses her devouring and raises her eyebrows at him. Dean’s only been holding his tumbler and a glance over to the tray, she can see that there isn’t any dessert on it for him, “You’re not having dessert?”

“Nah,” He says, “I’m not much of a dessert guy,”

“What?”

“Yeah,” He exhales, “I’m not much of a fancy dishes kinda guy anyway, but it’s hard if you grew up like that,”

“So, you’re telling me that you’d rather eat something simple than those magnificent dishes your chef creates?”

“Yep,”

“You’re weird,” 

“I know,” He chuckles, “But I’m glad you enjoy it. I’m sure the chef is delighted to have someone to cook for either,”

Y/N takes another spoonful, moaning and closing her eyes again and Dean shifts next to her. When she opens her eyes back up, he’s watching her with a smile on his face.

“Seriously, you’ve got to try this!” She digs into the mousse again and scoops up enough to hold it over to Dean. 

“Oh, no, I—,” He starts to say.

“Please? For me? You’ve got taste it,”

And she’s kind of pestering him, the spoon already brushing at his lips. 

“Come on,” She nudges the spoon to his lips, “I can’t be the only one to enjoy this tonight,” 

Dean rolls his eyes and sighs, but there’s a hint of a smirk playing along his lips, “Fine,” 

He opens his mouth and she pushes the spoon in. Dean's lips seal around the small silverware, and she pulls it out while his eyes are on hers. 

She feels flush, feels hot all of a sudden. It might have been more intimate than she thought it would be.

“And?” She asks and Dean nods his head.

“It’s good,”

“It’s good?” She frowns, “It’s fucking amazing!” 

He smiles.

  
  
  


*

  
  
  


After she devoured her dessert they stayed on the sofa and she emptied her glass of wine. And it’s not like she had planned it, but the wine makes her limbs feel heavy and her head light, and somehow, she ends up closer to Dean, laying her head on his shoulder. 

He lets her.

“You know, you did good tonight,” Dean says. She can feel his voice vibrating from his body. 

“Why thank you,” Y/N chuckles, “I’ll take that,”

“You should,” 

He nudges his shoulder up, making her lift her head and Dean takes the opportunity to drape his arm over the back of the couch so that it’ll be more comfortable for her. She doesn’t hesitate to curl herself into his side. She’s overly clingy when she drinks and she hopes he doesn’t mind.

While she looks out of the window, the lights blend into each other. 

“You know, I was wondering,” She starts to say and she doesn’t even know why she says it. It must be the wine speaking, “Have you ever had sex against the window in the dark?”

She can feel his body stiffen significantly. Dean inhales before he lets out an exhale with a chuckle, “How many glasses of wine did you have?”

“Eh, not much,”

“It seems to me like you’re a little tipsy,”

“Ugh, I am not,”

That’s a lie. She’s definitely tipsy. Maybe bordering on being drunk. She’s such a lightweight when it comes to alcohol, it’s a little embarrassing. 

“Right,” He’s still chuckling, “Thank you, by the way,”

Ah, he’s trying to steer the conversation away from the sex. She’s a little disappointed but well, if he doesn’t want to talk about something that’s fine. So, instead of pestering him, she asks, “Thank you for what?”

“For playing it so well. I really believed you liked me.” 

“Dean,” She pauses to look up at him, “I do like you.” 

“Yeah?”

Y/N lays her head back on his chest, “Yeah, you’re not a bad man, Dean. You certainly went out of your way to make it comfortable for my little family.”

“It’s the least I could have done considering you guys are giving up your life to help me out,”

“That counts as something in my book. And you know what?”

“What?”

She chuckles, “You’re funny,”

“I am?”

“Yeah, I don’t think you’re even trying to be but you are. The way you’re always grumpy, it’s kind of funny, to be honest,”

“Hey,” He protests, but he’s chuckling himself. 

“I like spending time with you,” 

“That’s good because I like spending time with you, too,” He says and his hand comes down from the edge of the couch to stroke along her arm. 

They stay like that for a while, both of them staring out the window wordlessly. She enjoys the silence with him, and she desperately tries not to think about him pressing her against the window and fucking her to the backdrop of the city lights. Nope. Totally not on her mind.

It’s when she feels her eyelids getting heavy that she pushes herself away from Dean and maybe she just imagines it, but there’s a subtle whine that comes out of this throat. He catches himself pretty quickly, though. 

“I’m going to bed,” Y/N says and stands up, feels his eyes on her when she rights her dress, “Unless you need me to be your fake fiancée longer,”

Dean smiles as he shakes his head, “No, I’m alright. Have a good night, Y/N. Sam will send you your schedule over,”

“‘K,” She nods, “Good night, Dean,”

  
  
  
  


*

  
  
  


Before she goes into her room, she checks in on Liv, sees the girl sleeping soundly. With a smile, she closes the door to her daughter’s room and makes her way to her own. 

There, she strips off her dress and gets herself ready for bed.

While she lays in bed, though, she can’t help but think about her weird day. If she’d tell Donna, the woman would think that she’s having a fever dream. 

Oh god, Donna.

Y/N grabs at her phone on the nightstand, looks at it for the first time after she has ditched it to go to dinner with Dean’s dad. 

There have been missed calls and texts from Donna, asking her when she’d be back or if she has been fired already because Y/N didn’t return.

Quickly she types in a message, maybe Donna’s asleep already anyway. 

> _ Y/N: You won’t believe what happened _
> 
> _ Donna: OH THANK GOD YOU’RE ALIVE _
> 
> _ Y/N: Shouldn’t you be sleeping? _
> 
> _ Donna: I was worried out of my mind _
> 
> _ Y/N: What happened after I made my way to the top floor? _
> 
> _ Donna: Oh god, you should have seen Raphael. He had to pack his things right away, but he was screaming and thrashing around, refusing to leave so they had to bring in security and had him thrown out of the building. _
> 
> _ Y/N: Wow _

Wow, indeed. Dean really fired him. On the fucking spot.

> _ Donna: The big boss believed you, right? _

She has to chuckle as she types in her next reply.

> _ Y/N: Well, he has to because I’m his fiancée. He proposed to me in his office. _

It’s a lie, but she has to keep up the illusion, doesn’t she? It’s best if Donna knows it, but only so much to feed into the illusion. She guesses she can explain it later when this will all be over. 

> _ Donna: WHAT THE FUCK  _
> 
> _ Donna: WHAT HAPPENED OH MY GOD TELL ME EVERYTHING _

She can’t help but laugh. 

> _ Y/N: I’m pretty tired, but let’s just say, I’ll let you know as soon as I can alright? Thought you’d like to know that Dean and I are an item now and that you’ll probably see my face in those glamour magazines. _
> 
> _ Donna: FUCK I’M SO JEALOUS _
> 
> _ Y/N: Right, I gotta get some shut eye, I’ll be in contact, Donna. Love you _
> 
> _ Donna: I love you too, Y/N, even though I’m fucking jealous. _

Still laughing, she places her phone back on the nightstand and curls herself into the soft pillows and comforter and it’s not long before she drifts into sleep.

**Notes for the Chapter:**

> Thank you for reading and commenting! It makes me super happy to see people liking what I put out!
> 
> Next chapter we'll get to see Dean interacting with Liv :)
> 
> I'm also on tumblr: @smol-and-grumpy


	8. Chapter 8

It's Thursday. It’s already the third day she’s been living in Dean’s penthouse, but there’s not a lot of time that she’s seen him. He probably has a tight schedule and is working hard. She guesses you don’t get to run a successful company when you’re sleeping. 

The morning after their dinner, they were sitting in the dining room to eat their breakfast and Dean made an appearance to greet everyone. He was all suited and booted, looking really yummy. She felt super underdressed showing up in her sleep shirt and sweatpants. He apologized that he was sorry he couldn’t meet them the evening before.

What stunned her the most was how he took his time with Olivia. Dean knelt beside the chair of the child to be on eye level with her, and produced a stuffed unicorn from his back with a bright smile on his face. Y/N eyes almost got teary from the gesture. 

“For your kingdom,” He said.

Olivia didn’t say anything, though. She just nodded, but clutched the unicorn close to her body. Dean sends her a grin when he gets back up, but instead of greeting Y/N, he went straight to Bobby and the old man scrambled out of his seat, still chewing on his bacon and eggs. 

They shook hands and she can tell that Bobby was impressed. He thought Dean was a snob, but obviously, Dean doesn’t act like one. That really fucks Bobby’s mind up, and she couldn’t help but grin to herself.

Before Dean left, though, he came back around the table to greet her, got on his haunches so he could look her in the eye. His hand goes to his jacket pocket, takes out a black card. 

“It’s yours now. Buy whatever you need for you and for your family, okay?”

“Dean, I can’t,” She started to say. She really couldn’t take it. He’s already paying so much and they really had all they need here.

“I want you to,” He said and nodded before he gets up, knocking on the table with his knuckles as he went, “Right, this penthouse is yours too, alright?” He didn’t specifically look at her, but he rather looked into the round of faces, “Please, feel at home,”

As she said, that was already three days ago and they haven’t seen him since and it’s totally weird because she gets paid for basically doing nothing and spending her days with her daughter. 

Bobby still goes out to work every day. He even dares to stay away longer, or go out for drinks with his friends because he doesn’t feel like he has to be around so much anymore and she likes that the old man is enjoying life. They have dragged him down for so long and he definitely deserves a break. 

Y/N and Olivia explored the whole penthouse already, except for Dean's room. She thinks it’s too private and she’d rather not break his trust. Even though she’s dying to know where Dean sleeps, wonders if he even sleeps at all. 

And even though she told Dean that she wouldn’t be using the card he gave her, she still did. But only to buy some decorative things for the penthouse. It’s too sterile for her taste. There are no plants or flowers, there’s just no life in it so she ordered some flowers and plants, set them up around the living room and hallway, bought some candles too to make the penthouse look cozier and less cold.

Dean’s staff are usually here from 6 AM to 6 PM. The chef can be requested to stay longer if needed. But the staff are all so nice to them, and Olivia started to talk to a couple of them as they help play along if Y/N and Liv are holding costume parties or play hide and seek. 

They have also used the pool once, but it was just too cold for Liv, and the staff seem to have noticed and told her that the pool can be heated up. They even showed her how to do it and by the time it had heated up enough, Liv didn’t feel like swimming anymore. Maybe it was Y/N’s fault too, since she forgot to pack Liv’s swimming ring and she’s just not a good swimmer yet. Y/N didn’t have a lot of time to teach her how to swim properly yet. She promised Liv to teach her next week — if they’re still going to be here, that is.

All signs point to yes. Since there’s no news about the lawyers finding out anything yet. 

She usually gets off pretty easily during the week, she thinks because rich people don’t like to gather during the week because of work, or maybe it’s just this week that Dean needs her to get accustomed to her new life first. She knows that there’s at least one social event lined up on the weekend, though.

In the afternoon, Sam sends her the appointment she has to attend. Something about social etiquette and while she frowned when she saw his message, Sam’s not entirely wrong. As the fiancée of Dean Winchester, she probably has to know how to behave in public.

So Y/N gets herself ready while Olivia is being tutored in her room by the teacher Dean has arranged for homeschooling. 

Before she leaves, though, she goes into her daughter’s room to say goodbye with the promise that she’ll be back soon. 

  
  
  
  


_______________________________________________________

  
  
  
  


Dean gets home around 6.00 PM which is exceptionally early on a Thursday. He’s thankful that there’s no event tonight, maybe he’ll get to calm down a little. All he actually wants to do is take a shower and sit down with a drink. Or maybe drink in the shower. Or taking a shower in a drink. It actually doesn’t matter as long as a shower and a drink is involved.

His tie is off as soon as he slips through the front door. The apartment is not as quiet as it usually is when he gets home late during the week.

While he walks along the freshly decorated hallway, which she did an excellent job with, he can’t lie about that, he can’t help but notice the sound. It sounds like it’s coming out of the living room. 

He’s totally not used to having someone in the living room. His guests usually stay in their wing. 

All the lights are on in the living room and his staff has already left. But there’s someone sitting on the couch in the living room, clutching a pillow to her chest as she watches a movie. The sound is loud and Dean walks around the couch and lets himself plop right next to Olivia.

“Hey, sweetheart,” Dean says, but the girl doesn’t react. It seems like the sound is too loud too, so Dean takes the remote and tunes the volume down a notch, “Why are you watching in here, huh?”

Not that he minds, honestly, he doesn’t. Not really. It’s just a little weird that there’s life in his penthouse after dark. It is usually just him and his thoughts. He doesn’t ask because he doesn’t want her to be here, he’s just really curious because they have a perfect set of TV in their own living room in their wing. 

The little girl tilts her head around, “The TV is bigger here,”

_ Ah _ . Of course. It’s also a very valid answer. He can’t even blame her, not that he wants to. 

Dean smiles as he takes off his suit jacket and drapes it over the back of the couch, “You know what? You’re right.” He looks around him, sees if maybe Bobby or Y/N are here but it seems like the little girl is all alone, “Where are the others, huh?”

“Bobby went out for a drink and Mommy’s still not back,”

“And they left you alone?” 

Olivia sends him a glare, “I’m six. Not two,”

Dean’s eyes widened. Ah. She’s six, not two. He has to suppress his laugh. 

“Who put the DVD in for you?”

“Missouri,” The girl says, “But she left right after,”

Yeah, Missouri usually has to take care of her grandkids on Thursday and Friday evenings. It’s a wonder she stayed so long, though.

“Well, princess,” He grins, and she starts to smile at the mention of the pet name. She obviously likes it, “I’m here now to keep you company, how does that sound?”

“You are the King here, you’re allowed to do whatever you please,” 

“Yes, I am,” Dean nods, wonders if Y/N fed that idea to her daughter, but again. She’s six, not two, so he guesses that Olivia’s quite bright, and she probably can put two and two together, even though Y/N might not have told her everything. “But as a King, I am keeping my kingdom happy so, would you give me the courtesy to watch the movie with you, princess?”

Her face lights up, “Yes, you may,” 

Dean thinks she’s adorable and it was after five minutes of making out what the movie is all about that he gets up and Olivia looks up at him, thinking he’d leave. But he has no intention of leaving. Instead, Dean asks, “Does the princess want popcorn with her movie?”

“Yes,” Liv says and nods her head. 

“I’ll be right up,” Dean walks to the kitchen.

“And a soda,” The girl says. 

“Aw, sweetheart,” Dean says as he stalls by the door into the kitchen, “I don’t think your Mom is going to like me giving you soda this late,”

“You mean the Queen,” She says. 

Dean is a little taken aback, but he keeps his face neutral. He nods, “Yes, the Queen will not be delighted to see me giving you sweet sugary soda,”

“That’s okay,” She giggles then, “Water is fine.”

“Water and popcorn, coming right up!”

He returns shortly with microwaved popcorn and bottled water. He wonders if it would be okay for him to get a couple fingers of whiskey, but he also thinks it might not be the best idea to drink when you are looking after a child. Not even when the girl insists that she’s six and not two. 

They sit side by side and Dean lets Liv tell him the story. It’s the Rapunzel movie. And Dean listens carefully, not interrupting and saying that he knows what Rapunzel is all about. The little girl gets all excited when she tells him about Rapunzel’s journey. She also sings along to all the songs and there are times where she buries her face into the pillow or alternatively after a warm-up phase, she buries her face into the side of Dean’s body and he really can’t help other than draping a protective arm around her. 

Dean remembers Y/N telling him that Liv doesn’t talk, but it seems like she talks plenty and she feels comfortable enough around him to lean against his side. He’s glad that the little girl opens up. It probably is not really easy for her to be pulled out of a familiar environment and being holed up in an unfamiliar castle. Although it’s safer than the place they used to live, Dean’s sure of that.

  
  
  
  


_______________________________________________________

  
  
  
  
  


Y/N’s running late. It’s almost eight, but traffic was really bad getting there so she turned up an hour late, stretching the meeting unnecessarily. The traffic is not better on the way back, even though she told Dean’s driver that he specifically has gotten for her that she needs to be home asap, as she wants to tuck Liv to bed. 

While she looks out of the window and watches the jamming of the cars around her, her phone vibrates in her purse.

Taking it out and looking at the screen, her blood freezes.

> _ J: I saw a pic of you with that dude _

Jimmy. 

_ Oh no. _

He’s the last person she wants to find out about it.

Donna had sent her the link to the article in which she was mentioned as Dean’s new fiancée, but there was no name, and there are a couple of pictures of them kissing in the store but her face is not really shown and she has no idea how Jimmy found out about it but he did. 

> _ Y/N: What do you want? _
> 
> _ J: You know what I want _

He wants money. What else. She wonders if he’s still working, not that it's any of her concern. 

> _ Y/N: I’m not married to him yet. I can’t give you any money. _
> 
> _ J: Find a way, honey. You know I can go to court and take away what you love most, right? _
> 
> _ Y/N: You will not touch a single hair on her head. We have an agreement. _
> 
> _ J: We do? Where does it say, huh? Can you have your lawyer send the copy over to mine, huh? Yeah, I don’t think so because there is no fucking contract, honey! She’s still mine and it seems like your new guy is fucking loaded. _

Fuck. She fucking knew she was naïve to not have their agreement written in ink on a piece of paper. But at that time, she just wanted out of it and didn’t have the time, nor the money to hire a lawyer to help her draw up a written agreement that she’s the sole custodian of Liv and that Jimmy will have nothing to do with them anymore. She should have known that he and his parents didn’t insist on it in order to have leverage against her. And it seems like his day has come.

> _ Y/N: Jimmy, leave it be. You didn’t have to pay a fucking cent all those years.  _
> 
> _ J: I’m afraid I can’t _

Her thumb hovers over the keyboard. She wants to type in something, wants to say  _ If you come knocking _ then but yeah, what then? She doesn’t know. 

She doesn’t know what to answer so she doesn’t.

> _ J: We can make a little deal. Your soon-to-be-husband likes deals, doesn’t he?  _
> 
> _ Y/N: Leave us alone. _
> 
> _ J: Just so you know, I can give you some time, that’s not a problem but if you haven’t decided when I think you should have decided, if you wait too long, then I’m coming for her. _

Her hands are shaking. She wants to answer but she just can’t. She doesn’t know what to answer. 

Maybe she can give him all the money she earns during this time. That would settle it. But she also knows that it would probably make Jimmy greedier, make him want even more. She doesn’t think she can win this.

  
  
  
  


*

  
  
  


When she arrives at the penthouse she can hear music coming from the living room. That’s going to be her first stop because she knows that music. It’s the music to the credits of Rapunzel. She’s watched it way too many times, knows it by heart.

She’s prepared to see Liv and maybe Bobby or one of the staff, but she’s not prepared to see Dean, still in his dress shirt and slacks. His sleeves are rolled up and his top three buttons lose. He’s slumped on the couch and Liv leans against him, resting her head on his stomach as both of them are sleeping soundly. 

There’s a grin on her face and she feels guilty knowing that she has to wake them up. 

Gently, she walks around the coffee table where Dean has his legs propped up. She picks up Liv, tries not to wake her up as she carries the girl. God, Liv has gotten heavy. It doesn’t happen often that she has to carry her child around. 

Even though she's being careful, Dean still stirs. He’s an awfully light sleeper.

“Hey,” He says and rubs over his face, pinches his eyes before he starts to blink the sleep away. He only notices then that the movie’s already long over, “I.. uh,”

She balances Liv across the room because she’s really too heavy for her to stall any longer. However, Dean’s quick to be by her side.

“Here, let me,” He says and he’s already lifting Liv off. The girl doesn’t even stir when Dean carries her, and Y/N can only watch as her daughter slumps in Dean’s arms. Her face is on his shoulder and there’s drool dripping onto his shirt. He doesn’t seem to mind and she’s sure that he feels it.

Y/N follows Dean as he walks along the long hallway to Liv’s room. They don’t talk. It’s not like words are needed right now. She’s still wound up and she rather just really be with her own thoughts. Besides, she doesn’t want to wake Liv up with their small talk. 

“Where?” He whispers as he pushes the door into her daughter’s room. 

“On the bed, I’ll get her bed ready,” 

Dean nods and walks up to the bed, lays Liv on it without disturbing the little girl’s sleep. 

“Right, good night, Y/N, I’ll see you tomorrow,” He still whispers.

She knows about tomorrow. They are having an outing and Pamela is coming over to help her choose the right dress. Apparently, Dean still doesn’t trust her choices enough. Not that she had a chance to prove it to him, so his doubts are probably valid. 

“Thanks, Dean, good night,” She says, even though she wants to ask him so much. She wants to ask him how his lawyers are coming along, wants to ask him if anyone knows about Liv, wants to ask him how long they’ll be staying here because it’s getting harder and harder for her to part from this place. 

She wants to, but she doesn’t. 

He nods before he slips out of the room and she hears his dress shoes clicking along the floor until they are out of earshot.

  
  
  
  


*

  
  
  


She made herself ready for bed too, thinking of having an early night, but there’s something nagging at her and so she makes her way to the living room on socked feet and in her sleep shirt that covers enough of her buttocks. 

Y/N finds Dean in his study. He has showered because she can smell the freshness hanging in the room. He’s sitting on the couch overlooking the city, nursing a tumbler of whiskey. 

When she gets closer, she notices Dean is wearing a white henley and sweatpants. That’s a first. She never thought that Dean even has comfortable clothes, to be honest.

“Hey,” She says as she comes to stand by the window. 

Dean looks up to her. His gaze rakes along her legs up to her face. 

“I just want to say thanks,” 

“For what?” Dean looks up and cocks an eyebrow at her.

“Being here for Liv when everyone was away,”

“Ah,” Dean snorts, “It’s no big deal. It was actually a pleasure,” 

“I thought Missouri would stay longer,”

“She had to take care of her grandkids, but really, Y/N, don’t worry. Nobody can get up here,”

“I know,” 

Dean looks up at her with a boyish grin. It doesn’t make him look so troubled, it doesn’t make him look as exhausted as he always is. His hand comes up, he touches hers. She’s standing close enough. His fingers play with the ring on her third finger.

“You’re wearing the ring,”

“Yeah,” She smiles, “I have to get used to it,”

He probably knows it’s a lie, but instead of embarrassing her, he pats the empty space next to him, “Sit down,”

She does, curls one of her legs up and pulls her shirt down so he wouldn’t see underneath.

“You want a drink?” Dean asks to which she shakes her head.

And while they sit in comfortable silence, Dean suddenly starts to chuckle.

“What’s so funny?” She asks.

“Your daughter tried to get a soda. Am I allowed to give her a soda? I mean, we probably have to lay down some rules that I need to follow,”

“She didn’t,”

Y/N is shocked.

“Did, too,” Dean nods.

“No, I mean, she talked to you?” 

He tilts his face to her, “Yeah, she was quite chatty,”

Wow. It usually takes so much longer for Liv to warm up to someone.

“You just have to tell her when she’s bothering you, okay? She knows that sometimes adults need some space,”

“Y/N,”

“Like, she knows that we’re not at home and she’s to follow rules here. Well, she has rules and home to but—”

“Y/N,” Dean says again, it comes out a low growl, “Would you stop babbling?”

“‘M sorry,” She says, “I’m nervous,”

He chuckles, “Really, when I said it’s my pleasure, I really mean it. I like her. She’s great.”

“That’s good then,”

Is it really? She doesn’t want Liv to get too attached to anyone at the moment. But she doesn’t voice her thoughts. Instead, she keeps them locked in and enjoys their comfortable silence, just watching the lights flicker in the distance. She definitely knows now why there’s a couch at the window. Dean probably spends his evening here often, just sitting, letting the day and week pass by, thinking and planning ahead. 

And there’s the thought about Jimmy again. About his threats. But Y/N knows better than to disturb the comfortable silence. Besides, it’s nothing that Dean should worry about. Jimmy’s her problem alone.

When she feels tired, she turns to him, “Guess, I’ll see you tomorrow,”

“Yeah,” Dean says and smirks. 

She can’t help but lean in, cups his face with one hand and places a kiss on his cheek. It could be wrong but she feels him leaning into the kiss, feels him inhaling and exhaling loudly. And when she parts, he tilts his head a little, letting his nose brush along her cheek briefly. His eyes are closed. Her heart is racing fast because she feels things she shouldn’t be feeling. But she pushes the feelings out of her mind.

Pulling away, she smiles, “Thank you again, Dean,”

He opens his eyes to smile back, “You’re welcome, sweetheart,”


	9. Chapter 9

“Rise and shine, sleepyhead!” Pamela comes into her room, pulls all the curtains aside and Y/N stirs, has to blink to get her eyes to adjust to the light spilling into the room. 

A glance over to the clock confirms that it’s almost 4 PM. 

She didn’t exactly  _ sleep _ that long. In fact, she went up in the morning, but her mind wouldn’t stop racing around Jimmy, and then, when Liv’s teacher arrived, she went into her room to take a nap because her head’s been pounding non stop since she woke up.

“How are you feeling?” Pamela asks as she sits down on the edge of her bed, “Here, you should take this. Bobby told me you’d gone to have a lie down because your head was hurting,” The woman holds out aspirin for her and bottled water.

“Thanks,” She says, “Doing better already,”

It’s not a lie. She still feels a little exhausted, but her head’s not hammering so hard anymore. Progress, she thinks. Hopes that with the aspirin, it’ll go away until she has to go to that charity event with Dean.

And that’s exactly why Pamela is here. She’s in the process of laying out more dresses at the foot of Y/N’s bed. Even though Y/N thinks that she has enough of those.

After swallowing her pill, she gets out of bed to give Pamela more room to work with. 

“What about this one?” The brown-haired woman asks, holding out a dress that’s really short and shows way too much cleavage. It’s barely a real dress, Y/N thinks, because the cleavage goes way down to the middle of her stomach. “We can pair it with necklaces that go down the front,”

Y/N thinks that her face gives it away that she doesn’t really like the dress. She has no problem with showing some legs, but a cleavage that goes way down to her stomach? She’s never been too confident with her own body, and especially not after giving birth to Olivia. There are some stretch marks here and there, not really something the public needs to see.

“Or, this one,” 

Pamela goes on and picks up another form-fitting dress, it’s strapless and navy blue and it has some kind of glittery fiber woven into it. Plus, it’s not that short either, at least a couple of inches longer than the other one she showed her. She absolutely hates to have her ass on display when she tries to sit down.

“Yeah, I like this one better,” Y/N says. 

“Well, I’ll leave you the two options. I don’t like the red one, to be honest,” Pamela looks back at the third and last dress, “I’ll leave you some necklaces and earrings for you to choose from,”

“Great,”

“Oh, I should also mention that Dean has picked out the navy blue dress,” The woman winks at her and there’s really nothing she can say, so she ignores the suspicious wink.

“Speaking of,” Y/N says instead, “Dean’s still at work, right? Do you know when I should be ready to meet him?”

Pamela lays out necklaces, compares them to the dresses as she answers, “He’s already here, he actually gave Bobby aspirin and asked if you’re okay,”

_ Oh. _

“Do you know where Olivia is?”

“I think she’s playing in her room. The teacher left two hours ago,”

“Right,” Y/N nods her head, “Do you need me right now because I want to go see my daughter.”

“No,” Pamela says absent-mindedly, “I’ll be back to put on finishing touches later after you showered and got dressed,”

“‘K,” She says and walks to the door.

It’s just a couple of steps to reach Liv’s room and as soon as she’s out of hers, Y/N can hear laughter coming out of it. There’s also male laughter and it doesn’t sound like it’s Bobby’s. 

The door’s open so she peeks in. As soon as she sees them, she starts to frown and there are just too many feelings inside and she doesn’t know how to sort them and pick out which feelings are right and which ones are wrong. 

Dean’s sitting in one of the small chairs at the table, a crown on his head and a couple of pink beaded necklaces around his neck. His suit jacket lays discarded on the floor, the sleeves of his white dress shirt are folded back and his tie hangs loosely around his neck. 

Olivia’s dressed up too. She wears a pink tutu over her normal jeans and she has a tiara balancing on her head that looks like it’s new, and she doesn’t think she’s seen the tutu before either. There are more beaded necklaces around her neck and some pink diamond bracelets around both her wrists. A couple of princess costumes are hanging from the castle and she wonders if Dean had bought Liv all this stuff. 

“Hey,” She slowly makes her way into the room, feeling like she’s intruding. 

“Mommy!” Liv squeals and runs towards her, hugs her around her waist.

“What are you guys doing?” She looks from her daughter to Dean who’s now sitting up a little straighter, but still on that ridiculously small chair. She smirks and thinks that she should take a picture, send it to all the glamour magazines, let the people see how Dean Winchester, the hottest entrepreneur of the year 2020, really is.

“I’m having a tea party with the King!” Olivia says excitedly as she jumps up and down, “Do you want to join, Mommy?” 

“Uh, I don’t know? I don’t want to intrude,” 

“You not, you’re the Queen so you can sit next to the King!” Olivia shouts out and already pulls her towards the little table, “Right, King?”

Dean grins as he sips on his imaginary tea, sticking his pinky out as he does. He sets the cup down, nodding his head, “That’s right, princess,”

Reluctantly, Y/N sits down and Liv is pouring her the imaginary tea. She takes a sip as Dean watches her. He looks absolutely comical with the beads around his neck and the crown on his head, but he doesn’t seem to mind. It blows her mind.

They sip their tea as Olivia dances around and performs a dance for the King and Queen of her little kingdom.

When her daughter is in her element, she tilts her head just slightly, whispers to Dean, “What are you doing?”

He cocks an eyebrow, “I’m having tea?” And to emphasize his words, he lifts up his miniature teacup and takes a sip.

“Dean,”

“Y/N,”

“Seriously,” She starts, “Why are you here in my daughter’s room having imaginary tea on a Friday afternoon?”

He frowns, “Because I like tea?” He holds up his cup and smirks, “And besides, she calls me handsome King. I must say it’s much better than icy King,”

“You know about your nickname?” She has to chuckle.

“There’s nothing I don’t know,”

“Do you know about the tabloids? I mean, have they found out about Liv?” God, she hopes she doesn’t sound too paranoid. He’s just really afraid that it has already leaked and Jimmy would somehow find out about them being here. Jesus, she’s an idiot, she doesn’t even know if Dean’s place is known to the tabloids? Do people know where he lives? If yes, would Jimmy come knocking? He wouldn’t get past security she supposes, but he would get into the building. 

The music stops in the background and Olivia bows. They both tear their eyes away from each other to clap their hands for the princess. The music starts again and the little girl slips into her next performance.

“Nothing leaked, Y/N. And really, I just want to get to know her, is all,” Dean whispers. 

She sends him a glare, “Why? You know you don’t have to. It’s not in our agreement,”

“I’m trying to figure you out, Y/N,” He says, it’s louder than a whisper, “I want to get to know you and by getting to know you past the things I already know, it’s also by getting to know your daughter because you come as a package deal.”

  
  
  


_______________________________________________________

  
  
  
  


And that’s the truth. He fucking knows that they come as a package deal and honest to god, he thinks that he sometimes has trouble reading Y/N, and maybe, just maybe, Dean thinks, if he understands Olivia, he might get a better understanding of Y/N as well. Because she’s been sending him mixed signals since last night where she got all sweet and friendly towards him but also, she seems so distant as if something’s troubling her. 

He also has such a fucking hard time to keep his hand off of her and needed all his fucking willpower not to just pulled her into his lap last night, make her dance on it and make her come more times than she ever has. 

Suffice to say, he was pretty hard after that kiss on the cheek she left him with. And it’s fucking embarrassing! A kiss. On the fucking cheek! He’s no fucking teen anymore goddammit. Kisses on the cheek shouldn’t turn him on and yet it fucking did. He had to beat himself off in his bed while he thought about all the kisses he shared with her, spilled his sticky seed all over his fucking stomach and coated his half pulled down underwear with his warm cum.

But somehow, after Dean said that he wanted to figure her out, she storms out of the room, and Dean scrambles after her, holds her back with his hand around her wrist and makes her turn around as he crowds her against the wall. 

“There’s clearly something upsetting you, Y/N,” Dean hisses, “You think I don’t notice, but I do. You’ve got to tell me, and let me help fix it. Is it because I took my time to watch a movie with Olivia? Or that I enjoy being a guest at her tea party? Did I overstep an invisible boundary?”

Her eyes are wide and he can see that she’s fighting with her tears, tries not to let them come out, it makes him feel uneasy. 

“It’s not you,”

“Then tell me what it is! Obviously, something’s troubling you and I can’t help fix it if I don’t know what there is to fix!”

“Dean,”

“Y/N,” Dean says a little softer, as he holds her chin between his thumb and forefinger, tilting her head up to look at him. Her eyes are glassy and Dean has to swallow before he speaks with concern in his voice, “I just want to help, okay? And I have the feeling that you’re holding something back,”

“I can’t,” She shakes her head, “Dean, it’s not something that concerns you or our deal, so don’t worry about it,”

“Forget the deal, alright?”

“Why should I forget it when I’m constantly reminded of it?” She fights back. 

He sighs, feeling somewhat defeated, “You know that’s not true,” 

“Dean,” She says again, “Don’t you think that I know that if your lawyers give you the green light to end our agreement tomorrow, you wouldn’t do it? You wouldn't need me anymore, therefore we would have to leave. I can’t let myself get attached to you, to this life, and I can’t let myself be dependent on you. And most of all, I can’t let Olivia get attached to it either,”

Wow. That kind of hurt. Dean can’t lie about it.

He drops his hand to his sides, feeling even more defeated, but he looks at her and the eyes that look back at him reflect his pain. 

“I would still help you, you know, despite the damn fucking contract,” His voice is soft. 

“Why would you?” She asks, the frown etches deeper in her face.

And Dean doesn’t know. He knows as well as her that the only reason he would help her is if it would benefit his company and everything beyond that, he would do it because he likes her, but he can’t let himself go there. Can’t really let himself admit it. Well,  _ he _ knows why he would help her despite the contact, his fucking heart knows it, his mind not so much. Instead of saying anything at all, he stays mum and he just knows that he’ll beat himself for it later.

“Right,” She says meekly, “What time should I meet you?”

He nods. It’s back to pretending. 

“Meet me at 6 PM at the front door.”

“‘K,” She says meekly and makes her way to her room. 

Dean returns back to the tea party, lets Olivia pour him another cup of imaginary tea and he watches as the little girl pours her stuffed animal tea as well. Dean watches her some more, taking a sip of his pretend tea every now and then. The girl is happy. She’s carefree. He doesn’t know, but he thinks that she is probably the happiest she’s ever been with having her mom to herself so often, even though Dean needs to steal her mom away for a couple of hours every other day, Dean still guesses that it’s better than having her mom working late hours five days a week. 

God, he wants to protect that. He feels the need to protect the child’s happiness, even if it’s not his child, and even if it is not his fucking concern. 

  
  
  


*

  
  
  
  


Dean waits nervously by the front door. He doesn’t even know why he’s so nervous. Thinks it’s because he doesn’t know if she’ll really show up, even though it’s in the contract, but the way she was so sad and disappointed today, he wasn’t sure if she’ll be up for it. 

He was also so close to telling her that she doesn’t have to come when she doesn’t feel like it, but he thought that maybe she would take that the wrong way and end up being madder than she already is.

So that brings him back to being nervous when he shouldn’t really be. 

There’s the clicking of heels in the distance and he sees her appearing from the guest living room where Liv and Bobby are probably in there watching TV. 

She wears  _ his  _ dress. Well, at least the dress he’s chosen for her and there’s a strange clenching of his heart when she walks towards him. There’s a hint of a smirk at the corner of her lips. Maybe she isn’t sad or mad anymore after all. Maybe she just needed time to get into the mood of going out. 

His breathing is a little uneven when she comes to a halt in front of him.

“You look lovely, Y/N,” He says, hoping she doesn’t hear how his voice comes out a little shaky. 

“You look sharp, loverboy,” She chuckles, and then she looks down on herself before she twirls around. He can’t take his eyes off her either, also not from her tits that almost want to escape, “It’s the dress you chose,”

“I can see that,” Dean smiles, “It looks great on you like I thought it would.”

She gets a little flustered. He thinks it’s cute.

Pulling her lips between her teeth, she bites down and it’s not fair because he knows how they feel and he fucking wants to bite down on them himself. 

“How long do we have to stay?” She asks and Dean has to laugh, loud and sharp. 

“We’re not even there and you already want to leave,” He teases and gets serious, “Seriously, we stay for the press to take a couple of pictures and I have to make sure the charity gets my cheque,”

Well, he thinks she’s really a girl after his taste because he hates those events too. Normally he’d just hand over his cheque, sit at the open bar while people would come to shake his hand and he’d leave drunk.

“Okay,”

“I will have to kiss you, you know that, right?” He asks, and he doesn’t know why he asks because she also knows that as it’s the whole reason they are going out in the first place.

“I know, I’m okay with it,” She smiles, “Also, I wouldn’t mind if you want to practice beforehand,” There’s a wink, and god, how can she be so fucking cute.

Dean has to hold himself back, wants to really keep it strictly business, for her sake, maybe more for his own sake. So he kills the mood a little, “We’ll see about that, sweetheart,”

“Ugh,” She lets out a playful groan. Dean thinks it’s somehow to demonstrate that it’s no big deal for her. And is it weird that he feels bad that she’s not disappointed more? It probably is. He doesn’t really know.

“Would it lift your spirit if I told you there’s an open bar?”

“Go on, I wanna hear more,” She whispers seductively and Dean has to grin.

He drops his voice, and says it more huskily, “Trays of hors d’oeuvres,” 

“Mmmhh,” She hums.

Dean leans close to whisper into her ear, making his voice extra low and gravelly, “Chocolate fountain,” 

“Oh my god, Dean,” She gasps, and they both start to laugh, “Is that true?”

Shrugging, he says, “I hope so. They usually have one,”

“Can we maybe stand around that chocolate fountain the whole night?” She jokes as she weaves her hand into his hooked arm as Dean opens the door for them. 

“We can do whatever you want, Y/N,” Dean says, the only difference is that he’s not joking at all.


	10. Chapter 10

They reach the venue of the charity event and already Y/N can see flashes of lights as they drive up to the entrance. Even the tinted windows of the limousine can’t keep the flashes away. Her heart starts to race when she realizes that this is it. This will be their first outing to the world as an engaged couple. 

“You ready?” Dean asks as the car comes to a halt. The back of his hand rubs against her arm gently.

She’s not. Not really. Somehow, she still thinks it’s a bad idea but also she sees money and security and a fucking future for Liv. And it’s too late to back out now but she’s definitely not ready yet.

“Ugh,” Y/N groans.

He chuckles, “Yeah, me neither,”

“You’re not?” She asks with a frown. 

How can he not be? From the way he walks, talks, and behaves, she thinks he loves those things because he’s always so in control, and is such a big personality when it comes to red carpets. She knows this because she’s been doing her research while she was bored off her mind in the penthouse. 

“Tell you a secret,” His hand goes from her arm to her thigh and strokes her as he moves closer, “I hate these events,”

She has to chuckle.

“Okay,” He squeezes her thighs, “Let’s get this over with, shall we?” His other hand is on the door handle, ready to push it open.

“Wait,” Her own hand grabs at his arm, “What happens when we get out?”

Dean stalls and turns to her, “There’s a red carpet. We walk it, smile for the camera, and then we go in,”

“And get a drink,”

He chuckles and nods, “And get a drink, or several,” 

She nods back, although she’s not ready at all but will she ever be? The only way is forward, she thinks, and takes the hand that Dean’s holding out for her to help her out of the car.

As soon as she gets out of the limousine, she’s blinded by flashlights. 

His hand comes around her waist, fingers squeezing her flesh as he pulls her closer to his body. She tries to smile, tries to keep her eyes open as the camera clicks and the lights flash around her. 

Dean steers her along the red carpet until they come to a halt before a backdrop of the name of the charity. 

His gaze is fixed ahead and he’s smiling, but he turns to her then smiling down at her. It’s his real smile that he gives her, the one she knows is genuine because it’s just a small one, his lips a little crooked. 

“Relax, you’re doing great,” He whispers and she nods back, smiles up at him as genuinely as he does, placing her palm on his chest lovingly.

Dean’s hand on the small of her back tightens as he pulls her closer, pressing her body into his side. His face moves closer, and there’s a raise of one eyebrow. It’s a question, she knows. A permission to go in for that kiss to show the world. Nodding her head subtly, she agrees, smirks just a little because her heart’s beating so fucking fast. Dean smiles back, as he comes closer and then she feels it. His soft lips on hers. It’s electrifying, even though it shouldn’t be.

The kiss is gentle, soft, nothing like the first kiss they shared. There’s also no tongue involved, but it doesn’t mean it makes her feel any less warm. Doesn’t mean the tingly feeling isn’t there between her thighs. He kisses her for a long time, moves further forward until she bends and then he tips her down, holding her as he presses his lips harder against her own.

He breaks the kiss and she’s ashamed of the whimper she lets out. Dean seems to have heard it, because he chuckles. He leaves his forehead on hers though, smiles at her as he pecks her lips once more before he pulls her upright again. He kisses her forehead after, leaves his lips lingering there too and she melts against him. And during the short romantic interlude, she forgets completely that the cameras are still shutting away. 

The moment is over pretty quick after that and he keeps his hand on her waist as he guides her inside. 

While they walk along to greet the host, Dean turns to her, squeezes her side, “You okay?” 

She looks up to him, chuckles as she sees that there’s lipstick on his lips. She stops walking to brush her thumb over his upper lip. Dean chuckles with her. 

“Yeah, I’m okay, what about you?”

“Good,” He says, “You were great,”

“Well, thank you,” She hooks her hand into the crook of his arm as they continue to walk, “I hope it was good enough.”

“Nah, it was pretty great,”

Y/N looks up, frowning and Dean fucking winks and before she can say anything more, they are standing in front of the host. 

  
  
  


*

  
  


While they stand by the side of the dance floor watching people dance, a waiter with a tray full of champagne flutes walk by and they grab one and Dean’s right, there are other waiters walking around with trays of hors d’oeuvres, but none of them walks close enough for her to grab a bite off the trays. 

Dean seems to have noticed because he disappeared for a while and came back with a big smile on his face while he balances a tray in his free hand. 

Dean Winchester, hottest entrepreneur of 2020 walks around with a stolen tray of hors d’oeuvres just because he knows that she wanted one. How’s that for a headline? Sounds pretty good to her. 

Y/N can’t stop laughing when he comes to stand next to her. She reaches out, wanting to take something off it when Dean pulls away with a frown.

She cocks an eyebrow at him, looking puzzled.

“If you want something you should get your own tray!”

He’s laughing when he holds the tray back to her, though. God, he’s cute when he’s funny. There’s not a trace of the icy King left. At least not for the moment.

Dean sets his empty flute in the tray and they stand there and eat the little delicious canapés off of it, and when a waiter with a tray of champagne flutes walks by, Dean holds him back and makes him stand right beside them as they both eat and drink. 

“You do that often?” She asks, as she swallows down a bite. 

“Not as often as I probably should have,” He shrugs and empties another flute. She joins him and it’s not long until the flutes on the tray are empty. The waiter asks Dean if he should get them more champagne. 

Dean eyes her up and down, and she nods her head enthusiastically. 

He chuckles, “I don’t know, you think you can handle more, baby? Or are you going to get drunk again?”

_ Baby.  _

He never called her that before and she guesses it’s only to keep the illusion, but she quite likes the term of endearment. Especially when it comes out of Dean’s mouth.

“Hey, I wasn’t drunk,” She frowns.

“Of course not,” He grins.

“So,” The young waiter asks, “Sir, do you want me to bring you more?” 

“I think we’re good, thank you,” Dean thanked the waiter and she pouts. 

“C’mon,” He leans down, brushes his nose against her cheek and he’s so fucking close. God, he smells so good. “Next up is the chocolate fountain, huh?”

That really helps to put a smile on her face and Dean offers her his arm which she gladly takes. 

Y/N’s thankful she did take his arm because her legs feel a bit wobbly. Maybe Dean was right after all. She’s a little tipsy and she didn’t even notice it until they started walking. From next to her, she hears a rumble, hears him laughing. He fucking knows.

They stand by the chocolate fountain now and Dean abandons her for just a moment to get a plate with fruits and two long sticks. She impales half a strawberry on the stick and holds it out, letting the chocolate coat the whole fruit before she sticks it into her mouth. Closing her eyes, she moans out loud as the taste of chocolate covered strawberry explodes on the tip of her tongue. The perfect mix between sweet and a little sour. 

Dean nudges his elbow against her arm and she sees him frowning when she opens her eyes again, “Do you want to get a room with that chocolate fountain?”

She snorts out a laugh, “Sorry, it’s so good! I never had it before!”

“Never?”

“No?” 

It’s not something that’s standing around in every corner of the street, is it? She only heard of it, but she has never seen or eaten off of it.

“Should we get one for the penthouse?” 

“What?” She laughs out loud, “You can’t be serious!”

He smiles, “I’m dead serious. I think Olivia would love it.”

His statement takes her by surprise. Dean thinks about Liv, even if he doesn’t really have to. 

“Yeah,” She agrees, “Liv would love it. She’d also not want to eat anything else,”

This time, she holds a grape in the fountain, takes a bite and cherishes the taste.

“What’s so bad about it?” Dean shrugs, “It is fruit after all,”

“You’re a bad influence,” She jokes and Dean’s eyes are on her face.

He’s not laughing, just staring at her.

“What?” She asks.

“You got something here,” His finger points at the corner of his mouth.

Her finger goes to her own mouth to brush it away, “Here?”

Dean laughs, “No, here,” His hand comes up, thumb brushing at the corner of her lips. 

He shows her the drop of chocolate on the pad of his thumb and her hand closes around his wrist, pulls his whole hand towards her face.

Y/N grins before she sucks his thumb into her mouth. Dean’s eyes widen and she might have heard wrong but she can swear that there’s a deep sound coming out of his throat as she lets her tongue swirl around his finger. 

His mouth opens and closes as he tries to push something past his lips, but before Dean can say anything, someone’s clearing their throat loudly next to them.

They are teared back to reality and turn around to see John Winchester.

“That’s quite the show you’re presenting us with,” The old Mr. Winchester scoffs, “But I see through you,”

“Dad,” Dean pulls his thumb out of her mouth, “It’s nice seeing you too,”

Y/N feels blood rushing to her head. What does he mean he sees right through them? Does he know? Oh god, she gets paranoid again.

“You will only get your shares when you marry, son,” John addresses Dean, and Dean only, “I doubt you’ll go that far, will you?”

There’s an awkward staring competition going on. Neither of them says another word and she feels out of place. 

She watches the stares, watches the frown on Dean’s face and when her eyes travel over to John, she sees the old man’s lips curve up and suddenly, Mr. Winchester Sr. is grinning.

“You know who’s here, son? Carmen. Maybe you should go back to her,”

Wow. He really has the audacity to say that when she’s standing right the fuck there!

“What?” Dean’s frown is getting deeper, “You don’t even like her!”

“At least she’s willing to sign a prenup,” John shrugs, and then he turns to her, “No offense, dear,” 

“Full offense taken!” Dean growls, and he sets the plate down on a tray of a waiter who happens to walk by and thank god he did because she was afraid he’d smash it on the ground, “C’mon, Y/N,” Dean takes her hand and pulls her along to the open bar. 

They find an empty bar stool and Dean pats it, makes her sit down, “Your feet must be killing you,”

He’s not wrong. The heels are torturous. 

Dean stands by her side, and he orders a flute of champagne for her while he orders something much stronger for himself. 

When he gets his drink, he turns around and sets the champagne in front of her.

She eyes him. She wanted something stronger.

“What?” He asks, but then he senses her displeasure, “You’ll thank me later, sweetheart. It’s better if you stick with one type of drink,”

Gah, she hates that he is right. 

He downs his drink in one go, orders another one straight away. 

Her hand goes to his shoulder, making him turn around.

“You okay?”

“I’m fine,” Dean answers. It comes out a little snappish.

Y/N can see that Dean clearly is  _ not _ fine. Dean downs his second drink as well, orders another one right up. 

“Hey, Dean,” She says. Her hand goes to his arm, jerks at it until he turns to her. His eyes are restless, and he’s trembling.

Reaching up, she cups his face with both her hands, her thumbs strokes his cheek, “You have to relax, okay?”

Dean closes his eyes, exhales loudly but she feels him giving into her touch, feels him letting himself calm down in her palms. 

“‘K,” He nods, “Yeah, oka—”

It’s a spur of the moment and she doesn’t think everything through, but she pulls his face down to hers, presses her lips to his. Dean is surprised, his lips slack against hers, but then she breathes relief when he kisses her back, presses even closer, his scruff rubbing against her delicate skin. 

They kiss without tongue, but she still tastes the whiskey on his lips. 

When she breaks the kiss, Dean pecks her once more, leaving his forehead on hers. His eyes are dark, and he looks at her like he could eat her alive and she knows, she just fucking knows that she would let him. 

“Let’s go home,” Y/N whispers, and he nods as he licks his lips. 

“Ah, look at the lovebirds!” A voice sounds from next to them, tearing through the comfortable silence they share.

Dean tilts his head to the side with her hands still cupping his face, “Sam,”

He straightens himself up and she pulls her hand back. Sam takes one of her hands and places a kiss on the back of it, flashes her one of his best smiles after.

“Hi, Sam,” She greets him. 

He looks sharp in his tux, but not as sharp as Dean. Maybe she’s biased.

“I was wondering if you would like to have a dance?” The tall man asks her.

“She doesn’t,” Dean says sharply before she can even answer. Not that she wanted a dance, but she’s capable of answering herself. “We’re leaving,”

“Yeah,” She nods in agreement and scrambles out of her stool. Dean’s hand is quick on her arm to help steady her. 

“I’ll see you tomorrow?” Sam asks Dean.

“Yeah, I’ll meet you at the club,” 

Club? She wonders what’s tomorrow because she doesn’t know of any plans. At least nothing she has to attend. 

“Oh, Carmen is here,” Sam says before they turn to leave.

“So I’ve been told,”

“You don’t want to see her?” The taller man asks with a playful grin on his face, even though Y/N guesses that he already knows the answer. Maybe Sam just really loves to pull at Dean’s legs. 

“I have no fucking interest in seeing that woman again in my life,” Dean states firmly and he weaves an arm around her waist as he starts to move, “Bye, Sam.”

Dean proceeds to guide her through the mass of people before she can even say goodbye to Sam.

Outside, the press is still there, but there were fewer flashes and it isn’t long until a limousine stops to take them home.

Letting her get in first, Dean sinks into the seat next to her. He rubs a hand along his face, threads it through his hair, exhaling loudly. His hair is all ruffled up when he lets the hand drop next to him.

“You okay?” She asks just to make sure. 

She has the feeling that there’s something troubling him and she doesn’t know what it is. Maybe it was his father? Maybe Sam? Maybe the fact that Carmen was there and he can’t have her back when Y/N’s still around? If that’s the case then she doesn’t understand because Dean could easily just ditch her, pay out the amount he owes her according to contract — which is a ridiculously small amount compared to his fortune — and get back with Carmen, get married, and finally get his shares. 

“Yeah,” He says and turns his head towards her.

“You always say that you’re okay and that you’re fine, but I know you aren’t,”

He chuckles, it’s all fake and she can hear that too, “Why shouldn’t I be okay?”

“Because I think that right now, you’re regretting hiring me because your ex-fiancée is back and she’s ready to take my place, but you can’t because I’m here,”

Dean frowns, “You really think that?”

He makes her second guess her thoughts. Now she’s frowning too.

“Yeah?” She shouts, “You can just tell me and I will leave, it’s really no big dea—”

“—Jesus Christ, Y/N, shut up!”

She gasps.

“That’s not the reason why I’m not doing so well,” His voice is softer after the outburst.

“It’s not?”

“No!” Dean growls annoyingly, “Fuck, I couldn’t care less about Carmen!”

“Then what is it?”

He drops his head back and rubs over his face with both his hands, threads them through his hair again before he smoothes it back. It’s really unfair that he can do whatever the fuck he wants with his face and hair and he still looks fucking good.

“I was having trouble sorting things out in my head. I just want to find out something,”

She frowns some more, “Find out what?”

His fingers play with the hem of her dress, “Can you move closer?”

Y/N does.

Dean drapes an arm around her back, his finger lazily playing with her naked shoulder, strokes and draws circles on it. She feels embarrassed that this little gesture already makes her feel all fuzzy. 

It’s a while before he speaks.

“Can I kiss you?” He whispers low.

It comes out of nowhere and she looks at him, sees that he’s not smiling, meaning that he’s serious.

“But we’re not in public?”

“Forget the public, forget the act, I just want to see if I’m right,”

“See if you’re right about what?” 

She’s so fucking confused and as she turns to face him, his free hand brushes against her face and goes to the back of her neck, thumb stroking her cheek.

“Can I?” He asks again, ignoring her question completely.

He licks his lips, and she can’t stop staring at them. And she just knows she can’t say no, so she nods as she pulls her lips between her teeth.

Dean doesn’t smirk, in fact he doesn’t show any emotions when she closes in. 

Then she feels them, his soft and damp lips on her own. It’s unlike the kiss they shared during the night. It’s gentle and soft and the tip of his tongue licks along her lip, begging to be let in and she grants it to him, parting her lips slightly. Dean’s tongue licks into her mouth, slides in beside hers as he pulls her even closer. She moans as his tongue delves deeper, making him swallow the sounds she makes.

The car comes to a halt and Dean breaks the kiss, making her whimper at the loss. She knows she should be ashamed about it. Ashamed of how affected she is by just one simple kiss. 

They stay close, the tip of his nose touches hers.

“Did you find out what you were looking for?” Y/N whispers out her question.

He nods and pulls away, “I found out more than I thought I would,” 

**Notes for the Chapter:**

> Oh my god.... what did Dean find out? ;)


	11. Chapter 11

_ Fuck. _

Dean’s fucked.

He isn’t supposed to feel all these things. He doesn’t even know what he feels, but it’s something he’s definitely not used to nor had he ever felt anything like it before.

And especially not for someone he fucking hired to be his fake fucking fiancée!

_ Fuck _ .

The elevator ride up to the penthouse is awkward to say the least. The tension is thick beyond belief. He could feel it hanging heavily between them, could cut it with a fucking knife or poke at it with his dick for that matter, because he’s fucking hard.

He hopes she doesn’t notice the huge bulge and it needs all of his will power not to just crowd her in and fuck her right here. He needs every ounce of self control he possesses not to make her come on his cock before they even reach the top floor. He wants to do all of that, of course. Dean doesn’t think he wanted anything more in his life. Well, that’s probably an exaggeration but it feels like it’s the truth right now. But he’s behaving because he knows that he fucking  _ can’t _ .

Dean really  _ wants it _ . He does. He wants to show her all the benefits of being fake engaged to him. Wants to show her things not even his previous girlfriends got to enjoy, because fuck, he’d be lying if he’d say that he felt all those things with anyone before. 

_ Jesus _ , he  _ wants _ so much. But he won’t. He fucking won’t because he can’t let himself go there. He wants to believe that it’s for her sake, but he’s selfish and he knows that denying himself for her is actually for his own fucking sake. 

And he swears, he fucking swears, that however close they get, he won’t fuck her. It’s a safety measure he’s holding up for himself. He’s afraid that if he would let himself fuck her, he would never be able to stop and they aren’t what they pretend to be.

Maybe he’s kidding himself. Because he fucking knows that he’s greedy, knows that he won’t be satisfied with just simple kisses, but goddammit, he wants to at least try. Nobody can fucking blame him for trying.

He’s lost in his thoughts when the elevator pings and Y/N scrambles out. Dean follows suit. 

Inside the apartment, she stalls and turns to him, “You don’t need me tonight, do you?”

_ Yes, I do _ . He wants to say, the words are sitting loosely on the tip of his tongue. But he doesn’t. Dean swallows them down. Instead, he lowers his gaze, shaking his head, “No, I don’t. Thank you.”

“Right,” She nods her head and he might be wrong, but there is a flash of a disappointment on her face that he detects before she turns away from him, “Good night, Dean,” 

She already begins to walk towards her room when Dean speaks.

“You were doing great, Y/N. Good night,”

Whipping her head back, she smiles. Dean replicates it.

When she disappears into her room, he lets out an exhale. Rubs his hand through his hair, scratching at his scruff as he walks towards his room. 

Once inside, he sheds his clothes and throws them carelessly into the hamper. Not that the tux needs to be washed after wearing it once, but Dean just really can’t be bothered to put it back on the hanger. 

A glance at the clock tells him that it’s not even 11 PM. He feels restless, his body feels on edge. Normally, when he’s feeling like this, he can easily call someone who’s more than willing to come spend a couple of hours with him. Not since Carmen, though, because contrary to people’s beliefs, when Dean’s in a relationship, he’s faithful, had always been. Well, he doesn’t want to call Carmen, even though he’s sure that she wouldn’t say no to him, but she’s been sleeping around and honestly, it disgusts him not knowing who’s been inside of her lately.

  
  
  


*

  
  


Dean’s in his study after having showered. He rubbed himself raw while the water washed his cum down the drain. This better not be a fucking habit because he doesn’t have the patience to jerk himself off every day because he gets hard when she so much as touches him. 

The clock struck twelve a couple of minutes ago, but the city is still lively and vibrant. He sees people on the street, cars driving around when he looks out of the window. 

He sits down with his whiskey, after having dressed in his sweats and henley. He thinks about how he should probably catch up on sleep, but sleep is a rare thing lately. Maybe if he drinks enough he will finally get a couple of hours in, who knows.

Another hour has passed in perfect silence when all of a sudden, he hears footsteps in the hallway. He usually never closes the door out of habit as he is normally the only one in the penthouse so late at night. 

The footsteps come closer. It sounds like someone is walking along the marble flooring on their bare feet.

He doesn’t look back when the footsteps come to a halt in front of the study. He doesn’t need to because Dean knows who they belong to. His heart picks up pace and his dick twitches as it fucking knows.

“Come in,” He says, his voice a little gravelly from the whiskey.

Y/N walks in and closes the door. 

Dean listens to the footsteps as they come closer, tilts his head to look up at her when she’s standing next to him.

Maybe he shouldn’t have looked, but again, that would be rude and he doesn’t want to be rude because he doesn’t hate her. He likes her way too much, and that’s not really good either. 

His heart skips for just a second and he has to will himself to keep on breathing. 

She’s standing there, wearing a silk cami set he knows he paid for because it was on the invoice he got from Garth, but he didn’t know what the set looked like. It’s also not like he cared that much about it at that moment. He just told Garth to add some sleepwear, underwear and what not to complete a whole wardrobe. 

Draped over her shoulder is a short silk bathrobe, but she didn’t tie it around her. Her nipples are poking at the silk of the cami top, and he can definitely not notice that. Wonders a little, how they would feel underneath his palm, or in between his fingers, or in his mouth.

He closes his mouth that is standing agape upon seeing her, swallows down the invisible lump in his throat, “Shouldn’t you be asleep?”

“Shouldn’t you?” The reply comes back immediately. She’s quite witty.

“Touché,” Dean chuckles lazily.

She flops herself down next to him, and Dean tries not to look at her tits that bounced on impact of her body hitting the couch. He failed, though.

While Y/N sits down, she brings a whiff of air down with her and he can smell the fresh tint of honey and something flowery. She’s showered and now he can’t stop wondering if she made herself come too. If she’s affected by him as much as he is by her. Probably not. Nobody is as pathetic as he is.

“Can’t sleep?” He asks as he takes another sip from his glass, tries to think of anything else than her perky nipples, but he realizes then that his glass is already empty. 

“No,” She looks over, watches him toy with his empty glass. He looks at her to see her sending him a knowing look, “You probably shouldn’t have more,”

She’s right, of course. He debates on getting more out of spite, but realizes that it’s pretty much a childish thing to do. But he really can’t think straight right now.

“Do you sleep? Like, at all?” She pulls her legs up on the couch and turns sideways, hugging her knees to her chest. Dean can see her bare legs, can see the back of her thighs. It shouldn’t turn him on.

“I rarely do,” He admits, “Why are you not sleeping?”

“I don’t know,” She shrugs, “Just feel like I don’t want to be alone. And I want to ask you something,”

He cocks an eyebrow, tilts his head a little to the side, “Ask me what?”

“You can say no,” She says and tucks a strand of hair behind her ear. Her face is flush, he can even see it in the dim light that’s filtering in through the window.

Say no? Yeah, like that would happen, he will fucking try to, yeah, but he’s weak and honestly, if she asks him to fuck her now, he doesn’t know if he would be able to resist.

“Go on,” Dean says, voice husky, and he waits with bated breath. 

“So, uh,” She stalls, like she’s not entirely sure, like she’s a little embarrassed because she’s also looking anywhere but at him. After a pause, she continues, “I was wondering if, you know,”

There’s that pause again and it drives him fucking nuts. 

“Y/N,” He says firmly, because he’s barely able to breathe right, “Are you going to say it today or.”

“No, no, okay, I’m… it’s just,” She pulls her lips between her teeth, bites down on it. He thinks it’s cute, but also it doesn’t help his state of mind at the moment because he would fucking like to bite on them himself. “Like,” She restarts, “Would it hurt for you to pretend in private too?”

Uh. That’s a tough question. It would hurt him yeah. It would especially hurt his fucking cock. Of course, Dean doesn’t say that. Instead, he asks, “What do you mean?” Because yeah, what does she mean?

“You know, I’m talking about touching, little kisses here and there,” Y/N is not looking at him but out of the window. She pauses again, but then she looks back at him, with that glint in her eyes, “I thought it would just be easier for me to pretend to the world when I can pretend in private too,”

It does make sense to him. A little at least. God, who is he kidding. 

He nods his head, “Uh-huh,” Pulling his own lips between his teeth, “Yeah, we can do that if it makes you feel better,”

“No,” She blurts out.

“No?” He asks with raised eyebrows, “You just said—”

“—Not only because _ I  _ would feel better, Dean. You would feel better too. I can still feel that you’re not comfortable and maybe it helps you as much as it helps me.”

_ Oh. _

Is he so obvious?

“You think I’m uncomfortable?” 

“Yeah?”

He has to chuckle. But she might be right, he should really try to relax more, “Okay, then let's do it,”

The smile she gives him is wide and white. It makes him smile with her.

Dean eyes her. The grip around his glass is tight and then he has an idea, so he grins, “C’mon,” He says and stands up, walks over to the sound system on his bare feet and pushes a button. He fishes his phone out of the pocket of his sweats, searches for a song to play, hits a button of a song that he’s last heard at the event tonight. 

Softly, the melody of Frank Sinatra’s _ The Way You Look Tonight _ starts to sound out of the speakers and Dean grins while he holds out a hand for her to take. 

Y/N laughs, “I can’t dance,” 

Even though she said it, she still lays her hand in his.

“C’mon, let me make up for holding you back from dancing with Sam,” He says, as he pulls her closer and weaves a hand around her waist. 

It’s somehow true. The reason why he didn’t want it was actually because he felt jealous. And it’s not something he’s ever felt before either. Not with any of his girlfriends before, not really with Carmen. When Sam asked her, Dean was immediately filled with a confusing protectiveness. With more confusing possessiveness. He never felt possessive with other women, maybe he knew that they would stay no matter what. Y/N though, she’s not like any girl he’s met. That’s what he once told Sam, and it’s true. With her, he knows that she would leave him if he wouldn’t treat her right, contract or not, she would walk away. She’s passionate and her sense of morality is not compromised. 

And maybe, Dean thinks, that’s exactly why he’s so scared of this. He’s scared of losing control, losing himself and he’s normally always in control.

He pushes his thoughts aside as he guides her, her one hand on his shoulder, his other hand on the small of her back as he pulls her closer. Their bodies press against each other, her tits feel soft and warm against him.

She laughs, as Frank Sinatra continues to sing, their bare feet make tapping noises on the floor. 

> _ Yes, you’re lovely, with your smile so warm _
> 
> _ And your cheeks so soft _
> 
> _ There is nothing for me but to love you _
> 
> _ And the way you look tonight _
> 
> _ With each word your tenderness grows _
> 
> _ Tearin’ my fear apart _
> 
> _ And that laugh, wrinkles your nose _
> 
> _ Touches my foolish heart _

By the time the song finishes, she presses the side of her face to his chest and he’s afraid that she’d hear how hard his heart is beating. But then he feels her pressing her body closer to his and it’s only fair that her heart beats as fast as his does. He smirks when he feels it.

The next song starts to play automatically, Eric Clapton’s  _ Wonderful Tonight _ . 

> _ We go to a party and everyone turns to see _
> 
> _ This beautiful lady that’s walking around with me. _
> 
> _ And then she asks me, “Do you feel alright?” _
> 
> _ And I say, “Yes, I feel wonderful tonight.” _

When the song is almost finished, he can feel her body relax in his grip and can feel her head getting heavier on his chest.

“You tired, hm?”

She yawns and nuzzles her face against his chest some more and Dean has to chuckle, “C’mon, let me get you to bed,”

“Nuh-uh,”

“No?”

“No, wanna stay here,”

He lets out another chuckle.

“Okay, c’mon,” He lifts her up and she wraps her arms around his neck and her legs around his body. Dean proceeds to walk to the couch with her in his arms. He tries not to touch her ass, but it’s almost not possible. And he can’t lie that it feels so fucking great in his palm.

She lays her head on his shoulder, nuzzles her face into the crook of his neck as he carries her over. Her hot breath fans over his skin, makes the hair on the back of his head stand up. 

When he arrives at the couch, he lays himself down, positions her on top of him. There’s really not much space. He’s going to let her fall asleep properly and then he'll tuck her into her own bed. 

At least that’s the plan. 

He plants a kiss on the top of her head, “Is that okay?”

“Mmmh,” She hums and kisses his neck. 

It’s only his neck, but it shouldn’t make him feel the things he feels. 

“Y/N?”

“Huh?” She’s almost drifting off already.

“I’m not going to fuck you,”

“‘K,”

He doesn’t really know why he says it. Maybe as a precaution. Perhaps he doesn’t want her to feel like he’s taking advantage. And perhaps, he’s a little disappointed that she doesn’t protest. But honestly, he didn’t expect anything else. She’s not like the other girls who throw themselves at him. 

Dean strokes her back as he listens to her breathing even out, listens to the beating of her heart that gets slower. He closes his own eyes as sleep overcomes him.


	12. Chapter 12

The sun shine’s bright against the window as Y/N wakes the next day in an unfamiliar place. She pushes herself up, sees that Dean’s still lying under her. 

_ Oh god. _

The realization hits her and her memories start to come back.

They slept on the couch together. 

And she spilled out that she wanted to be more intimate with him in private. 

Ugh. Even though she stands by her statement, it still makes her cringe.

Y/N remembers that she was so afraid of telling him all that, was afraid that he’d say no. Thankfully, he didn’t. And she made up a reason too. Gave him a believable explanation. Well, the real reason is pretty simple, she reckons. She’s touch-starved. That must be it. That’s what she’s telling herself. 

Dean’s still sleeping peacefully, his face slack, his lips slightly parted. He looks soft. It almost pains her that she has to wake him up. It’s almost 9 AM according to the grandfather clock next to the bookshelf. She’s not sure of his plans for the day, but Dean’s normally up pretty early and she’d hate for him to miss a meeting or appointment if he has any. 

Nuzzling her face back into the crook of his neck, she kisses along his throat, kisses up to his jaw, places more kisses on his cheek and the corner of his lips.

He stirs, and at the same time, she feels something getting hard too. She has to chuckle at that. She felt it last night already and god, she can feel that Dean’s dick must be big. Not that she’s has seen many to compare it with. There was Adam who she lost her virginity to, back in high school. That one was certainly not impressive. Then there were Cole and Gabriel back in college before she met Jimmy. Neither one of them really made a lasting impression and she doubts that she would have stayed with Jimmy if it hasn’t been for Olivia. And then, after Olivia her sex life was non-existent.

“Mmhh,” Dean hums. A smirk plays along his lips.

“Wake up, sleepyhead,” She whispers softly. She kisses his cheek again and Dean slowly blinks his eyes open. 

“Wow,” He huffs out, “Could get used to waking up like this.”

Y/N feels blood rushing to her face hearing him say things like that. Apparently, Carmen didn’t even live here. At least that’s what Missouri told her. The woman told Y/N that she is the first woman who has ever stayed over. And even though Dean has this fancy guest wing, he never had guests who stayed longer than one night.

“You’re poking me,” She lets out a soft chuckle, and then she gets up, sees the outline of his hard cock through his sweatpants, and has to bite down on her lip. It’s bigger when she sees it in daylight. And maybe it’s good that he doesn’t want to fuck her because she doesn’t even know if it’d fit. “Have you got no self-control, Dean?” She teases him. She’s always pulling jokes when she’s nervous and honestly, seeing how big he is definitely makes her nervous.

He sits up, rubs the sleep out of his eyes and over his face. And he isn’t even trying to hide his morning wood. Dean looks at her, frowns a little, “Oh, sweetheart, I have self-control, alright, otherwise we wouldn’t have just slept last night,”

_ Oh. _

She tries to change the subject, feels like she would go too far if she’d be asking why he held himself back. Well, to be fair, she probably wouldn’t have said no to him, honestly. But Dean made it clear that he’s not going to fuck her for whatever reason, so she respects that, too. And she tries not to think about if she would be able to change his mind.

“Did you sleep well?” Y/N asks instead of all the other things going on in her mind.

Dean still rubs at his eyes and he stops to look at her. He doesn’t say anything though and it’s as if he’s thinking hard about the question she asked.

“Yeah,” He answers after a while, “I slept very well. I haven’t slept that well in forever,”

She smiles, “Good,” 

He sits upright and she stands up, wants to go get dressed and most likely Liv is already awake. When she walks past him, Dean reaches out. His hand closes around her wrist and he tugs her down to him forcefully, sending her landing in his lap. He manhandles her so she sits sideways on top of him. She tries not to think of how good it feels to sit in his lap. How she feels like she belongs here. Dean’s erection pokes away at the back of her thigh. He doesn’t seem to care about it. Maybe she shouldn’t care either, but it’s quite distracting.

Nuzzling his nose against her temple, he places a kiss there. It seems natural, not like he’s pretending. It makes her blood circulate faster in her veins.

“How did you sleep?” His voice is still a little hoarse from sleep. It sounds sexy as hell. It sends tingles down between her thighs. His scruff is a day's worth longer, it prickles just right.

“Good,” She says, it’s the only thing she can say. Her heart is beating so fucking fast, feels warm all over.

“We should do it again sometime,” Dean suggests. He makes it sound so easy, so  _ normal _ .

“Yeah,” She agrees too quickly because yes, she’d like that too.  _ Maybe next time in a bed _ , she thinks, but doesn’t say.

“Thank you,” He places a kiss on her forehead and then proceeds to stand up with her still in his arms before setting her down. 

Frowning, she looks up at him and Dean grins before he bends down and kisses her forehead again. It’s the little gestures that make her knees weak. How does he know that she absolutely loves forehead kisses?

“For what?” She asks, because it came out of nowhere.

“For the good night’s sleep, I needed it,”

  
  
  


*

  
  
  


He’s been away at the club — which turned out to be the golf club and not a nightclub — the whole day, and there’s not much going on except for some people coming to take the couch out of Dean’s study and replace it with a bigger one. It’s the couch they spent the night on. She wondered why Dean wanted it out because the old one was still good and comfy. Perhaps it bears the memory? Maybe the memory of their night together pains him? Although it didn’t seem like it when he woke up under her.

Whatever it is, she couldn’t dwell on it, as she has a day full of taking care of Liv ahead of her and the little girl is the best distraction.

After the staff goes home, Y/N is baking cookies with Liv.

It’s a great pastime and they both loved to do it in their old apartment. They do it in the main kitchen, because it’s just so much bigger.

“Where’s Dean?” The girl asks as she steals a chocolate chip from the bowl. 

“I don’t know, honey. Why are you asking?”

“I miss him,” Is the answer. “It’s Saturday, is he working?”

Well, Dean always works, no? Y/N pegs him down for the guy who rarely rests. 

“I don’t know,” 

The girl sighs, “I like Dean,”

Cocking her eyebrow, she looks at her daughter, “You do?”

“Yeah,” Liv smiles, “He’s different, he takes his time with me,”

“Yeah, he told me that you’ve talked to him. That’s progress, honey. I like how you’re opening yourself more.”

“Mommy, he isn’t like anyone else. He’s Dean,” The girl slides off her stool and goes to stand in the middle of the living room as she begins to sway to the music.

Yeah. He’s Dean. It’s as simple as that. Dean is different and that might not be a good thing.

Liv is dressed in her princess costume and dancing to the music of Frozen when Y/N prepares the cookie batter. Oliva will decorate it with chocolate chips and sprinkles once Y/N’s done.

They already managed to get one tray in the oven and the smell of the cookies slowly fills the living room.

Y/N is standing by the kitchen island and is in the middle of scooping up the dough, placing little cookie portions onto the second baking tray. She’s being watched by Liv who is sitting at the island, nibbling away at some dough. The little girl tries to be subtle with it because Y/N doesn’t like to see her stealing dough, always telling Liv that the girl is going to spoil her appetite for the real cookies if she keeps on eating the dough. 

She knows of course that her daughter is snacking, but she decides to let it slide for once. Maybe because it didn’t matter today. She made so much batter thinking that she’ll bake more for the house staff as well. Some kind of thank you for enduring her and her daughter for almost a week, since she knows that it’s clearly not in their job description.

The front door opens. Olivia immediately leaps out of her seat and runs to see who it is. It should scare Y/N, since she doesn’t know if Jimmy knows where they are yet.

“Hey, Liv! Come back! You’re not finished decorating!” Y/N calls out for her daughter and is about to dart after the child but all she hears back is laughter. Relief washes over her. 

There’s a laughter that’s rumbling deep and one that clearly belongs to a little girl giggling.

“You okay, princess?” Dean asks her daughter as he walks into the living room with Liv perched on one of his shoulders. The little girl still laughs and squeals.

Dean stalls at the entrance to the living room as his eyes travel to the kitchen and her. One of his arms is still holding Olivia perched on his shoulder, his long and thick fingers tickling her. The little girl squirms and tries to wind out of his grip.

He’s wearing his golf clothes. A short sleeved shirt that hugs his strong biceps. It’s different from his suits, a little more casual. Still hot, though. She doesn’t think there’s anything that could make Dean look bad.

“It smells delicious,” Dean smiles.

“We’re baking cook—” Liv starts to say but can’t finish the sentence as she giggles again when Dean’s fingers start to tickle her.

Y/N chuckles upon hearing her child’s laughter. It’s so genuine, so carefree.

“Why are you laughing, princess?” Dean asks as he makes his way over to the kitchen island, his fingers are restless on the little girls back, “What are you baking?”

“De—” Liv lets out a squeal of laughter.

“What?” He asks.

Olivia is trying to wind herself out of his grip, squirms and snakes, and Dean chuckles as he sets her down onto the stool at the isle. He sits down next to Liv.

She watches with a grin as her daughter catches back her breath breathing. The hiccupy laughter slowly dies down. The girl is panting hard, tears streaking the corner of her eyes. Y/N knows that her daughter is absolutely happy. Maybe it’s the happiest she’s been in what seems like forever.

“Cookies!” Olivia shouts out the answer to Dean’s question as soon as she can breathe normal again. 

“That’s awesome! Can I help, princess?” He asks Liv, nudges at her with his elbow, and the girl is more than delighted, nodding her head frantically. 

“Right,” He stands up, “I’ll go wash my hands, princess. Don’t start without me, okay?”

Dean has long legs and is already halfway across the living room.

“We won’t, King!” The little girl calls after him.

Y/N thinks it’s probably too late now to not let Liv get attached. Seeing how happy she is when Dean’s playing with her. It’s bad, isn’t it? Super bad. It’ll be harder for them once they have to pack their things and leave, because somehow, Dean has found a way into both their hearts. 

  
  
  


*

  
  


While Y/N is preparing another tray and Olivia dances around, Dean walks into the living room. He’s dressed in a simple black t-shirt, some grey sweatpants hung low around his hips. And she tries, tries so hard not to look at his impressive package that the sweats do nothing to conceal. One could think he does it deliberately. Maybe he did. She probably has to step up her game as well. 

His hair is still damp and she guesses that he took a shower in record time so as not to make Liv wait for him for too long.

The little girl squealed and is on him again, jumps up to climb him like a tree and Dean laughs.

“Liv,” She says in a warning tone, “You should maybe give him a breather,”

“It’s okay, Y/N. I don’t mind,” Dean carries Liv over to the kitchen island and sets her down on a stool, taking the one next to her daughter. He looks at her with a boyish smirk that decorates his face. He looks much younger like this. Looks like a normal person and not the hot tycoon who smiles back at her from all the HD pictures out of magazines. “So, what do I have to do?” 

The girl proceeds to teach Dean what to do, which is to decorate the cookies with chocolate chips and sprinkles.

Dean apparently thinks it’s funny to line up the chocolate chips to make the cookie smile, using too many chips in the process.

“Dean, no,” She frowns.

He looks at her while Liv giggles, “Why, Dean, yes!”

She rolls her eyes, “You’re throwing off the chocolate chip/cookie balance. It’s going to be uneven!”

Popping a couple of chocolate chips into his mouth, he shrugs as he turns to face a still laughing Liv who’s doing her best at placing the chips on the dough to make it look even, “Is your mom always so uptight?”

Olivia sends him a side eye.

“‘K, don’t answer that,” Dean chuckles, “Don’t want you to get into trouble, princess,”

“I’m not,” Y/N scoffs, “I just like my cookies to be even,”

“Mommy, you are way too strict with Dean,” Liv chimes in, “It’s his first time, no one can do it right on their first try,”

“Exactly!” Dean slams his palm on the island, “Thank you, princess!” 

Still chuckling, he turns to face her, wriggles with his eyebrows and she can’t roll her eyes to the back of her head far enough. 

  
  
  


*

  
  


While they wait for the cookies to be done baking, Olivia watches Rapunzel again. Y/N cleans the kitchen and even Dean helps her.

“You know you don’t have to do this, right?” She asks as Dean is drying off the bowl she cleaned. Maybe she should have elaborated, but she has the feeling that Dean knows what she means. He doesn’t have to play along, he doesn’t have to spend time with them. 

Instead of answering her, he places the bowl back into the pantry. When he comes back, Dean cocks his eyebrow at her, “You know that you don’t have to clean either, right?”

“Yeah, but I want to,” She answers.

“Exactly why I do it,” Dean nods at her, sends her a warm smile before he joins Liv on the couch.

  
  
  


*

  
  
  


When the cookies are ready, she carries a plate over to the couch, sets it down on the coffee table and brings Liv her glass of milk. The girl should be having something real for dinner instead of just cookies, but she lets it slide because Liv was looking forward to the cookies the whole day already. 

She sits on the couch next to her daughter and Olivia slides down to sit on the floor, knowing that Y/N doesn’t like it if there are cookie crumbles everywhere. 

Dean picks up two cookies from the plate, hands her one. It’s one of his, with way too much chocolate and it looks like the cookie is trying to eat her with its big chocolate grin instead of the other way around.

Y/N takes a bite, the still warm chocolate melts on her tongue and there’s a chocolate string that attaches her mouth to the cookie as she pulls it away. She can’t help but moan a little because well, she really loves food.

She tries not to notice Dean’s chuckle. He probably does so from watching her devour her cookie. With a shake of his head and a smile on his lips, he takes a bite off of his own. 

Breaking the string with her finger, she scoops it and pushes it into her mouth and sucks the chocolate off of her finger. 

There’s a sound that comes out of Dean, comes out from the depths of his throat. It sounds more like an animal died there than anything else. She snorts out a laugh, but Dean’s not laughing. Instead, he munches grumpily at his cookie.

Olivia is eating and watching her movie, oblivious to what is happening. Or so it seems.

Dean grabs a cookie from the plate and breaks it in half because it’s the second to last one. He obviously wants to keep the last for Olivia. She almost wants to tell him that she has so many more, but he’s already holding out the broken off piece for her to take.

When she takes it, Dean turns to her. Immediately, he frowns. 

“What?” She asks, her own face starts to frown.

“Jesus, Y/N,” Dean growls, “You have chocolate up to your cheeks! How is that even possible?”

_ Oh. _

“Mommy always has chocolate on her face when she eats it,” Olivia turns around and grins brightly, her own mouth covered with chocolate.

He snorts out a laugh, “Is that so, princess?”

“Ya!” Liv doesn’t waste her time on them though, turns back around and starts to eat the last cookie on the plate and Y/N munches at her half too.

“Like mother, like daughter, huh?” Dean cocks an eyebrow at her and she smirks at him, with her mouth full of the bite of cookie.

He quickly pushes his half into his mouth before he reaches out to rub his thumb at her cheek close by her cheekbones, where there’s apparent chocolate. 

His thumb rubs at her skin and then he shows her the pad of it. She already moves her hand to wrap around his wrist, wanting to repeat what she did at the charity event, just to rile him up, but Dean’s quicker. He jerks his hand away from her, sucks his thumb into his own mouth, smirks around it. 

She wonders if it’s a self-defense mechanism because he doesn’t want to see her sucking on his thumb again. It must be because that sound that came out of his throat before was really a little embarrassing.

After that, Dean drapes his arm over the back of the couch as an invitation, jerks his head subtly but with that playful grin playing along on his lips, and she goes in willingly, resting her head on his shoulder. 

He relaxes under her, his shoulders sagging a little and the hand that’s draped over the back of the couch comes down to circle around her body.

It’s weird to even think that, but as they watch the movie together, it feels like they are a little family. And she knows, she fucking knows that it won’t last. But it also doesn’t hurt to enjoy the moment, right? Right.

Y/N closes her eyes just for a brief moment. Enjoys Liv’s laughter and enjoys Dean’s even breathing. 


	13. Chapter 13

It’s about ten minutes after Y/N laid her head on Dean’s shoulder that he felt her body slump. She fell asleep in his arms and Dean was so close to following her into her sleep. However, he wills himself to stay awake, repositions her, and reaches out for a pillow. He lays her head on the pillow on his lap. His hand still stroked her hips slightly, thumb mindlessly drawing circles on her leggings. 

Olivia starts to gasp when Flynn gets stabbed. 

“Mommy! Flynn!” The girl shouts out, and it blows Dean's mind that Liv’s still watching something so intensely and gets all riled up when she has seen the movie countless times before. That’s the magic of children, he guesses. A magic he’d like to protect. At least when they are still living in his kingdom.

As the girl doesn’t hear anything from her mom, she turns around to see and Dean places a finger to his lips, signaling for her that she shouldn’t be as loud. 

“Is she sleeping?”

“Yeah,” Dean chuckles, “We should let her sleep, huh?”

“Yeah,” Liv agrees.

“We’ll finish the movie, okay? Then I think it’s time for bed, princess,”

Her eyes narrow. Dean wonders if he’d said something wrong.

“Mommy always let me stay up as late as I want to,” 

Wow. Dean does his best to suppress his laugh. She really thinks Dean would let her get away with it. Well, he can’t really blame her for trying. He would have done the same probably. He still remembers the babysitter who had to endure him. 

“Is that so?” Dean challenges her, cocks one eyebrow for the effect.

“Yeah?” The girl says, not so sure anymore. 

It’s the way he looks, he supposes. People get intimidated. It’s apparently working on little girls as well.

“Princess, I can’t blame you for trying, but you’re going to go to bed after the movie. Unless,” He trails off, pauses for the effect.

“Unless what?” There’s a cute little frown between her eyebrows. Like mother, like daughter indeed.

“Unless you want the Queen to be mad at the King when she finds out that I let the princess stay up for as long as she likes,”

Olivia purses her lips together into a thin line, as if she’s thinking of her options. She exhales after a couple of seconds, “Fine,”

Dean smiles.

  
  
  


*

  
  
  


Dean scoops Y/N off the couch after he has put her daughter to bed and she stirs in his grip. 

Her face rests against his chest as Dean proceeds to carry her along the hallway, stirring some more with the motions of his strides. Sure enough, when Dean looks down, he’s met by her sleepy eyes. 

“Dean?”

“Yeah,”

“What are you doing?” Her body tenses in his grip. She tries to move but he’s holding her tight.

“I’m carrying you to bed,” He says matter of factly, making it sound easy.

After a couple of seconds, she starts to relax back in his grip. Y/N exhales before she wraps her arms around his neck and nuzzles her face into the crook of it, giving in to her tired state. Dean doesn’t lie when he says that he loves that. The nuzzling into his neck. It’s something new. His previous girlfriends didn’t do that. Or rather, he didn’t let them do it because it’s not something he’s ever felt comfortable with. The closeness in particular. It’s also not something he thought he’d like. To be fair, it’s something he never thought he’d need until now.

“I don’t wanna go to bed,” She breathes against his neck, hot air fanning over his skin. It sends a shiver down his spine, making his dick twitch in his sweats. It really shouldn’t make him feel anything at all.

He’s surprised, but deep down, he really hoped she’d say this.

“No?” 

“Nah,”

Dean chuckles, “Then I know just the place,”

Her body starts to get tense while he rounds up the corner and she gasps, “Olivia!” Suddenly, she’s alert, her motherly instincts kick in.

“Relax, I already put her to bed,” Dean calms her down and he steps into his study, walks over to the new couch.

“You did?” She’s staring up at him then, a slight frown playing along her forehead. She looks cuter than her daughter.

“Yeah,” Dean sits on the couch with her still in his arms. He lays himself down and pulls her back flush against his front. The view of the lit-up skyline is breathtaking. He still thinks it’s a privilege to be living here with this magnificent view. 

When he first moved up here, he thought he had it all. Now, though, there’s something nagging at him. He’s living in the city. Alone, and even though he’s surrounded by people, he doesn’t feel like he belongs. His late mother always wanted to move out of the city, get a decent place with a garden. Dad never wanted to, so he stayed in the city, and only moved mom to a townhouse. It was a big one and mom had a lot of space. There was a little garden, but it’s not what mom wanted. Nonetheless, what he has is something that he worked very hard for.

Maybe, Dean thinks, it’s a privilege to have her in his arms. A privilege that he might have to work harder for if he wants to keep it. Something he might even have to fight for. At least against his inner demons. 

Her head is resting on his outstretched arm, his other hand holding her by her hips. 

“She let you put her to bed?”

“Well,” Dean lays his face to the back of her head, inhales her scent, “She’s something, let me tell you,”

Y/N chuckles.

“She told me that you let her stay up as long as she likes,” He mumbles against her hair, “And then she wanted me to believe that you don’t care if she brushes her teeth or not.”

“Yeah,” She laughs, “That sounds like Liv,”

“She sounds like you,” Dean says.

“How?”

“You don’t seem like you like to be bossed around either,”

She turns around in his grip and Dean comes face to face with her. And even though he bought a new couch which is bigger than the last one, they are barely using half of it because she presses her body to his and he’s not letting go either. Her hand comes up to cup his cheek, her thumb strokes along his too long stubble. He couldn’t be bothered to shave today. 

“Sorry, didn’t shave,” He mumbles with a playful smirk. 

He doesn’t really know why he said it. It’s as if somehow he wants to apologize before they even kissed. Not that he thinks she’d kiss him. Even though he would maybe want it. Well, who is he kidding? He’s been waiting for a kiss since he woke up with her in his arms. She said they should pretend in private, but Dean’s never sure how far he can go and it just seems easier if he let her take the lead. So, now he’s here, being totally excited for a simple kiss. It’s pathetic.

“No,” She shakes her head, and she smiles a little smile, “I like it,”

“You do?” 

“Yeah, it makes you look soft,”

“Hey!” Dean growls and she giggles.

“You are, Dean. You’re a good guy.”

“I’m all hard and cold,”

“Olivia wouldn’t warm up to you if you weren’t good. She wouldn’t let you tuck her to bed, she wouldn’t want to spend time with you at all.”

It shouldn’t hurt him, but it does. Not because Olivia trusts him, but the thing that hurts is more the fact that Olivia probably has to go through so much at such a young age. It’s something that left a scar on her heart. It’s not right and that’s rich coming from a guy who bends and breaks rules sometimes to get a good deal. 

“Thank you,” She says and Dean’s grip tightens a little more around her. She sends him a warm smile and then she bites down on her lip.

“What is it?"

“Can—, I mean,” Y/N starts to say before she pauses, “Can I, uh, kiss you?”

His heart is doing something weird. Like it’s totally out of tune. Trips and falls like it’s drunk. Dean chuckles as he tries to keep his emotions casual.

“Y/N, you asked me if we could pretend and I agreed, didn’t I?”

“Yeah?”

“So, yeah, you’re allowed to kiss me any time.” He makes it sound so fucking easy. Like it’s only her who wants it and he doesn’t even know why. Maybe it’s to keep his defences up, some kind of a facade. Something that’s slowly crumbling. 

Still with her lips pulled between her teeth, she nods and when she closes in on him, she pops her lips out. It’s shiny and wet. He helps her too, surges forward, just a little, assuring her that it’s okay. His heart drums some weird beat in his ribcage.

The moment her soft lips meet his is like no other, and that’s what he likes about it. Every kiss with her feels special. It feels like they’re doing it for the first time, feels like something new. Dean melts against the kiss, his heartbeat slows down too. It’s as if her kiss manages to calm him, manages to signal to his body that  _ this  _ is familiar. 

The tip of her tongue traces along his bottom lip. Dean grins before he parts his own lips to let her in. It’s soft at first, gentle, like they need to get accustomed first, even though it feels like it’s the most natural thing. 

Her hand is around his face, gripping him harder as she pulls him into her, Dean’s hand in her hair. The kiss grows heavy, fucking needy, and there’s not enough air to breathe, but it’s not like they need it right now. 

She drapes her one leg over his middle and moves closer. Dean’s fucking hard, he can’t hide that and is sure that she can feel it too. It’s hard to hide anything in the sweats he’s wearing.

Dean can’t help that his one hand that’s on the back of her neck travels down her back, the tip of his fingers digging into her flesh on its way down.

“Jesus, Y/N,” He lets out a faint groan when he feels her soft ass in his palm. 

He also can’t help to squeeze it, shakes it in his hand but she doesn’t seem to mind if the sound she lets out into his mouth is anything to go by. 

There’s another sound that leaves his mouth and she takes the opportunity, sucks in his whole damn tongue, making him groan out loudly, making him forget his own goddamn name. 

She tries to drive her crotch to him, squirms as she searches for friction, lets out whimpers that go straight to his fucking cock.

“Do you need something, sweetheart?” Dean whispers. It comes out low, a little shaky, needy in his own way as his spit slick lips brush against hers. 

Instead of answering, she kisses him again, bites on his lips too, making him groan out and she swallows all the sound he makes. 

Dean knows exactly what she needs and he fucking knows that he needs it too. He can’t let himself go there though. He had told her that he’s not going to fuck her. But it's not fucking, right? If he can keep his dick in his pants, and still give her what she needs right now, that’s not wrong, is it? He’s not going to fuck her, at least not with his dick, and he stands by it. 

His walls are crumbling. 

He breaks the kiss with a tug to her lips, biting afterward, hard, sharp, hurting her a little. Maybe that was too much already? Maybe she doesn’t want it anymore. Perhaps, deep down in his subconsciousness, that’s his plan all along. Dean doesn’t even know if she’d be up to his antics in bed. Thinks she’s too good of a girl and all he would do is corrupt her. He doesn’t know if she’d let him. 

But instead of pulling away, she fucking bites back, grinds her hips further against his groin and Dean can’t keep the groan in his throat. It makes an escape.

“Fuck,” He breathes out and tugs at her lips again just to make sure. 

It’s absurd that Y/N would totally let him corrupt her. She would totally take whatever he’s giving her. She’d let him eat her up, spit her out. She’d let him break her and place the pieces back together after. The fact that she’s willing to let him do things to her doesn’t sit quite right with Dean, but he can’t lie that the knowledge drives him absolutely wild. His dick strains painfully against his underwear. He’s sure he’s leaking.

“Dean,” She whines.

“Tell me, what do you need, baby, huh?” 

He swears, he didn’t plan on calling her baby. It slipped out on its own. He thinks it fits. 

“I—, I,” She stammers, but she isn’t stopping her grinding.

He has to chuckle at the neediness she shows. Is a little surprised she can be like this. Not that Dean minds, though. He likes them like this, likes them even more if they beg. Maybe she will one day. He hopes she will. 

Dean pecks her nose before he speaks, “I know, baby, I know,” Because he does. He just knows what she needs and he’d never be able to forgive himself if he’d deny her — and by proxy himself — of this.

“You’re needy, ain’t ya?” He whispers low and dark.

“Uh-huh,” Y/N nods shamelessly. Dean wishes there was more light so he could see the flush of her cheeks.

“When was the last time you’ve gotten yourself off?” 

His hand that’s on her ass works its way around to the front, slips under her shirt to palm at her stomach as he waits for the answer he’s not even sure will come. She’s a good girl, he doubts she’ll tell him.

“Last night,” She mumbles and buries her face into his neck. 

_ Shit. _

He did too. The memories of him standing in the shower with one hand around his cock as his cum washed down the drain flashes in front of his eyes. 

“But,” She says, her hips still working. His hand on her stomach inches lower, the tip of his finger dips into the waistband of her leggings and panties. Only teasing. “It didn’t work. And the day before too, but it didn’t work either,”

Dean inhales sharply. 

_ Jesus Christ _ . That’s why she’s so needy. 

“Why didn’t it work?” 

“Can only come with my toy. Didn’t take it with me,”

_ Oh, goddammit _ . His dick twitches violently. Maybe she’s not as innocent as he thought she was. 

“You need me to help you out, huh?” 

He waits for the answer with bated breath. The tips of his fingers dip a little further down, tracing circles on her soft skin there underneath her leggings.

“Uh-huh,” Her face is still pressed into his neck. Her voice comes out a mumble.

“Baby, look at me,”

She does. Albeit reluctantly. She’s probably ashamed, he knows, but god, he just wants to look her in the eyes.

Her lips are between her teeth as she looks at him. There’s something in her eyes. He’s looking for that glint that tells him that she really wants it and he thinks he has found what he’s looking for.

He kisses her again gently but pulls away after, leaves her chasing his mouth and he has to chuckle. “Eyes on me, okay? I wanna see your reaction,”

“Yeah,” She nods. 

“Good girl,” Dean grins.

Y/N pulls her lips between her teeth again as he dips his fingers lower, has to bite back a groan as he feels her clit. She parts her legs some more, granting his hand better access. 

The pads of his fingers circle her clit, eliciting a choked squeal from her lips. His fingers thread down her slit,  _ and fuck _ , he bites the inner of his cheek so as not to cry out too loud at the wetness he finds there.

Dean swallows. 

“Jesus, baby, you’re dripping,” 

She nods.

This middle finger goes to her entrance, scoops up slick and spreads it all around. It’s slippery wet when he glides his fingers through her slit again to rub at her clit.

“Mmh,” She hums. 

It spurs him on knowing that he does it right for her.

“‘S that okay?” He leans his forehead on hers, pecks her lips. His breathing is ragged.

Y/N smiles. Giggles a little, “Fuck, yes,”

He smiles with her, kisses her again, longer, harder, deeper. 

And then he goes in, dips his finger into her pussy. It goes in easy, she’s so fucking wet but it’s so tight like he imagined it would be. He feels her clenching around his single digit immediately. The feeling almost makes him choke on his own saliva. 

“Christ, baby, you’re so fucking wet. God, tight too,” 

Dean's voice comes out a low growl, he so fucking wishes she would clench around his cock instead of his fingers. But he doubts that he will even fit. Well, he would make it fit, but he will probably die once he’ll be fully inside. It would be a good death, he reckons. The best way to go. 

Her smiling face twists in beautiful agony when he pushes in another finger, a frown playing along her forehead. 

He curves his fingers right, making her squeal in delight. Dean chuckles, seldom do girls laugh and giggle during sex with him, and this is just the foreplay, but she’s a fucking delight already. He can’t help but wonder how it’ll be when he fucks her. Because he wants that. Wants her laughing, wants her giggling but also he wants her begging.

Dean claims her mouth, breathes out while he slides his tongue along hers. Kisses her as deep as his fingers fuck into her cunt. He sucks on her tongue, making her moan into his mouth and he drinks in the sounds as if they keep him alive.

Her hips keep moving and she eagerly fucks herself on his fingers. He makes sure that the heel of his hand presses against her clit for extra stimulation.

“That’s it,” Dean whispers when he breaks the kiss to breathe, “Fuck yourself on my fingers, baby. Just like that, good girl,”

There’s a clench around his digits at the mention of her being a good girl. 

_ Ah. _

She’s  _ that  _ kinda girl. The best of the girls.

The clenching doesn’t stop and  _ fuck _ , it’s a tight fit even for his two fingers. He kind of doesn’t want to think about his dick in her cunt because if he does, he’s sure he will come instantly and that would definitely be embarrassing. 

“You’re close, baby, ain’t cha? Your pussy grips so hard around my fucking fingers, Y/N. Goddammit,” His breath comes out uneven.

“Fuck,” She nods her head frantically, closes her eyes as her pussy squeezes at him.

“Look at me,” Dean growls and bites at her lips, reminding her. 

When she does, he chuckles, kisses her nose, “Good girl,”

There’s the clench again. 

“You’re such a good girl, baby. Come, can you come for me, huh?”

The sound of his fingers hooking into her pussywalls as he fucks her is obscene. He practically slaps the heel of his hands against her clit with every thrust of his digits. It’s fucking filthy and wet and it’s actually the fucking best.

Her eyes narrow, the frown etched deeper into her face. But her eyes are on him like he told her to. Her eyelids start to flutter and she fights to keep on looking at him as her cunt starts to clench and throb around his fingers. 

Y/N lets out a squeal in delight, begins to laugh after. She’s so fucking cute when she comes, he almost feels bad for wanting to corrupt her. 

“Fucking beautiful when you come around my fingers, baby,” He whispers and kisses her roughly. Bites her too just to hear the squeal again. 

Dean lets her ride out her orgasm, her legs trembling and her clit gets sensitive at his touch. 

“You okay?” He asks as he pecks her lips and she grins against him.

“Yeah, oh god, yes,”

He chuckles.

He pulls his finger out from her underwear and leggings and they come out fucking drenched. He groans at the sight. It’s the best fucking thing. Knowing how wet she gets makes his cock throb. He’s so hard he could pound nails.

Dean brushes his hand at his sweats but not his fingers. No, he’d like to taste. As he said before, he’s a fucking masochist and likes to torture himself.

She sets her leg back down from around him as he places his fingers in between their faces. The heady scent of her cum is strong and intoxicating. 

He keeps eye contact as he sucks his finger into his mouth, twirls his tongue around them and she bites on her bottom lip. 

“You ever tasted yourself?”

Y/N shakes her head.

Grinning, he surges forward, kisses her deep, making her moan into his mouth when she tastes herself on the tip of his tongue.

“Fucking delicious,” He growls when he parts. 

During the kiss, she draped her leg around his waist again and Dean chuckles because she’s a needy thing and tries to buckle her hips up to feel his hard cock. God knows he wants that too, but he won’t give in.

Dean manhandles her around easily, lays his hand on her waist to keep her from squirming. 

“Dean,” She gasps, “I—, you—,”

“Nuh-uh,” He whispers against her ear before he buries his face into the back of her neck. 

“No?”

“Not gonna fuck you, Y/N,” He mumbles, tries to believe it himself.

She lets out a breath as if she’s disappointed. He doesn’t know if she is because he can’t see her face.

“Let’s just sleep, okay?”

She stops squirming and he lets go of her hips to wrap his hand around her body. Dean inhales her smell and closes his eyes as she lays her hand on his on the front of her stomach.

“Okay,” She whispers and pulls his hand tighter around her. 

**Notes for the Chapter:**

> Thank you so much for reading and commenting! I appreciate every one of you :) xx


	14. Chapter 14

Y/N’s sitting at the breakfast table. Her hands are shaking and she tries her best not to show. 

This morning, everything was great. She woke up next to Dean, nuzzled her face into the crook of his neck and placed kisses all over his throat and jaw to wake him up. He did so with a smile, telling her that he could definitely get used to waking up like this. And again, she avoided looking at his morning wood. 

_ God _ , he made her come so fucking hard. She doesn’t recount the last time she came so hard and with a big grin on her face. 

Usually, it was just her and her vibrator and even then she had to make it quick. It was more a chore to relieve herself than anything else. The walls of her apartments were thin and she was too afraid to wake Liv up. Was actually too paranoid and felt guilty about having a little bit of fun and finding relief when her child was sleeping next door. 

It’s not like she did it often. Maybe once a month if time and circumstances allow. It had been years since she'd last been on a date, even longer than that she had kissed someone other than Dean and the last man who had ever touched her was Jimmy.

When she actually wanted to return the favor, Dean wouldn’t let her. He turned her around and even though he was still hard, he was adamant about not fucking her. It’s was not really the fucking she wanted. She just wanted to help him like he helped her, but he wouldn’t let it happen.

She was both relieved and a little disappointed. Because yeah, she’s super happy Dean’s a real gentleman and doesn’t want for it to go too far, but also there’s disappointment because now that she’s experienced his kisses, his touches, his fucking fingers, she doesn’t know if she can resist wanting it again. Doesn’t know if she will be able to resist wanting  _ more _ .

But that’s not why her hands are trembling. No. The reason why she’s all over the place is the fact that as soon as she got back into her room, there were messages on her phone. Apart from the one from Donna sending her pictures of her and Dean’s outing, there were messages from Jimmy, asking her if she’d talked to Dean yet. 

Of course she hadn’t. She wouldn’t even know where to start. And it’s fucking sad that she can’t even tell Jimmy that this whole relationship is fucking  _ fake _ !

She answered that he should give her more time. 

The reason why she still can’t stop shaking is that her phone lights up next to her breakfast plate. 

> _ J: It shouldn’t be hard asking your billionaire fiancé to fork over some dough for me, to keep your daughter, no? _
> 
> _ Y/N: How much money are we talking about?  _
> 
> _ J: I was thinking about a million. I could ask more, but I don’t wanna be too greedy. _

Wow. She was thinking of paying him out herself, but there’s no way she can pay him a fucking million dollars. 

> _ Y/N: Give me more time _
> 
> _ J: You better hurry or else I’m coming for her _

She knows exactly who  _ she  _ is. Jimmy should definitely give her more time. Maybe if Dean can find the loophole soon, she can tell Jimmy that it was all just a fucking farce and he won’t pursue Liv anymore. 

But again, that would mean that she has to go back to her shoebox of an apartment, back to her life where there’s only her and Liv. 

When she tries to pick up her cup of coffee again, her hands are shaking so bad that she knocks it over, sending coffee spilling over the table. 

“Goddammit!” Y/N shouts out.

Good thing that Olivia is in her own room, and doesn’t hear her swearing. Liv would give her a hard time for saying inappropriate things and she just knows that she would lash out at the girl who would tease her about it, even though it’s not Liv’s fault.

Sure enough, Olivia walks into the room, “What happened?”

“Nothing, honey. I just spilled coffee,” 

The maid’s already here with a cloth, but Y/N takes it from the woman’s hand, cleans it up herself. It’s not like they are paid to clean up their messes. All they are paid for is to cater to Dean and not them. So, at the very least, she can help around here.

When she looks up from the table to glance at her daughter, she can see that Liv’s dressed in yet another princess costume Y/N has never seen. And she clutches a Ken doll which is dressed as a King. 

These things are all new. She hasn’t seen them when she made up Liv’s room yesterday. 

She hands the dirty cloth back to the maid when Olivia walks around the table to stand by her side.

“Liv, where did you get the doll from? Was it in your room?”

“Nuh-uh,” The girl shakes her head. 

“No?”

“Dean brought it up and this new costume. Isn’t it pretty?” The little girl smiles as she twirls around. It’s a cloud of pink, reminding her of cotton candy. 

“He shouldn’t spoil you that much. Did you at least say thank you?”

“I like spoiling her,” The deep voice comes from the door to the dining room. Dean leans against the door frame, dressed in a gym shirt and shorts. 

Yeah, she remembers him telling her that he’s going to work out with Sam and will be back before they have to head out for an opening of a new library his company helped fund. 

“Well, please don’t,” She snaps and stands up. They have to be ready to leave in an hour and she’d like to get some alone time in order to get herself into the right headspace to pretend. 

Her words might have come out a little too harsh and it’s not even his fault that she’s so all over the place. The fact is still, that she doesn’t want Liv to get used to getting gifts all the fucking time. She will never be able to match that once she’s back to her old life. The life she doesn’t even want to go back to anymore, and she’s upset that it fucking upsets her.

She leaves Liv where she is. The little girl knows how Y/N can be when she’s upset so Liv goes to sit with Bobby. The old man knows that he has to act as a buffer like he always did since she came back to live with him. 

Y/N also doesn’t need long to calm herself. She just needs a fucking breather. 

Pushing past Dean, he looks after her and she hopes that he doesn’t follow. 

“Hey,” It rumbles from the back and sure enough, Dean dashes after her. 

It’s not what she fucking needs right now.

She walks faster, but her legs aren’t as long as his. 

Dean’s hand is around her wrist, pulls at it and makes her turn around with force. Her back hits the wall in the hallway and Dean boxes her in, one hand braced on the wall next to her face, his other hand on her arm.

His gaze is hard and stern. His brows knit together and he’s so close. His freckles are visible, his scent clouds her mind. 

“What are you so upset about?” 

“It’s nothing,” She answers sharply.

Dean snorts, “Yeah, right.” 

“I have to get myself ready, Dean,”

“The hell you will!” He growls, “Y/N, if it upsets you that I’m spoiling Liv, then just tell me, but don’t go around being mad about it. I can’t fix things if I don’t know if I’ve done anything wrong!”

“I told you already,” She exhales and tries to keep her tears at bay, tries to swallow them so they won’t come to the surface, “There’s nothing. I just don’t want her getting attached. We’re out of here soon, I don’t want you spoiling her more,”

“Who said you will?”

“You made it perfectly clear,”

“Jesus fucking Christ, Y/N,” Dean pushes himself away from the wall and rubs a hand over his face, “Sam said they haven’t found a way out yet, okay? It looks like you’re stuck with me a little longer,” He looks back to her, a safe distance away and he looks a little pained. “And even so, who said that I will stop caring about Liv? Stop caring for you?”

She’s afraid to ask what he means. Afraid to let her mind go there. They’ve known each other for a week. Had maybe seen each other half of that time. It’s not healthy to get attached. Especially not to Dean and his blown up ego.

Instead of saying anything more, she pushes her way to her room, leaving Dean standing puzzled in the hallway.

  
  
  


*

  
  


Y/N wears the first dress she finds in her closet, which is a plain yellow wrap dress with a sweetheart neckline. It’s the opening of a library, she doesn’t have to go all out for it, but still, she wears high heels that she knows will hurt her feet. Not because he wants to, but because that’s how the public thinks Dean’s fiancée should look like. And besides, there’s this bet she has with him. She can’t lose because she’s having an off day. She signed a stupid contract that tells her to act like it and she always holds her end of the bargain. The ring is still on her finger, she wears it constantly. As a reminder maybe. It should remind her that there’s a contract between them. It serves as a reminder to act like she loves him. Just that maybe, it’s not really an act anymore. 

Dean’s already waiting in his study. He’s dressed a little more casual. He’s still wearing a designer suit but he has ditched his tie. Even the casual look makes him look like he just walked out of a photo shoot of a magazine spread and somehow, it fuels the troubled feeling in her guts. He doesn’t even have to try and still he looks fucking flawless. She doubts that  _ anyone  _ will really be suitable as his fiancée because somehow Dean manages to let anyone next to him look hideous. 

Liv’s in there too and they sit together by the little table in the back, a game of chess spread out between them. It seems like Dean’s teaching Olivia how to play. 

“Wow, Mommy!” Olivia cries out and slides out of the chair, abandoning her game to run towards Y/N. The girl buries her face into her sides as she hugs her. “You look beautiful!”

Dean stands up too, clears his throat before he strides over to where they are standing, his hand in his pockets.

“She’s right,” He says, “You look lovely,”

Y/N feels the blood rush to her head and she quickly regains her composure. She’s really not used to receiving compliments apart from the ones she gets from her daughter. She never knows how to act. 

“Who’s winning?” She asks instead. 

He smiles and takes a look back at the chess game, “I’d say me, but Liv invented her own rules, so it’s pretty much a draw.”

“I’m winning!” The girl says and sticks her tongue out to Dean. He replicates it. It looks absolutely comical and it helps. Helps to get her mind off the nightmare she encountered this morning.

“Right, Liv,” Dean kneels down to be on eye level with her daughter, “I’m gonna borrow your mom for a bit, okay?”

The girl pouts a little, “You always get to go out, but I don’t,” 

Dean glances up at her and she shrugs. It’s true. They have been holed up here for a week and even though it’s never boring because of the endless possibilities, she thinks that Liv needs a change of scenery. 

“Where would you like to go, huh?” He asks and Liv purses her lips and looks around the room as she thinks of an answer.

“Amusement park!” It comes out loud and clear.

They both have to grin. 

“Amusement park it is. I promise I’ll take you there, okay?” Dean says and boops Liv’s nose with his index finger. Olivia seems to be happy with that promise and Y/N just hopes that he doesn’t dare to disappoint a six year old. “You ready?” Dean asks when he stands back up. 

“Yeah,”

He eyes her up and down, “I think there’s something missing,” 

She cocks an eyebrow, “What?”

He digs in his pant pocket, pulls out a necklace. It’s golden, and has the same shape of diamond on it as the ring she’s wearing.

Dean smiles, “Turn around,”

“Dean, I don’t think I can—” 

“—Turn around, Y/N,” He says it again, more firmly and reluctantly. She does. 

He places the necklace around her neck, secures it in the back and she turns back to him when she’s wearing it. 

“Now, it’s perfect,” He grins smugly. 

  
  
  


*

  
  
  


Dean has informed her on the drive over that there’s going to be press and he’d have to give some interviews. All she has to do is to look nice for the pictures. His voice is a little off, like it pains him a little to tell her all that.

They took the obligatory picture as they stood in front of the new library. They also share a kiss, but it’s nothing like they shared in private. He has an arm around her waist as he leads her up the stairs and into the library where other press are waiting for him.

“Mr. Winchester? Over here,” Some PR man who was hired for this event calls out for Dean and is ready to whisk him away, but Dean stalls with his hand still around her waist.

“Will you be okay? I won’t be long,” He whispers with concern on his face.

She doesn’t get it. It’s not like he has to care what happens with her. She’s paid to do this.  _ He  _ pays her to do this. 

“Of course,” She smiles, “Go get them, tiger,” 

It’s all forced. She’s still not in the right headspace and she guesses that he must know it. Damn him for being so intuitive. 

Y/N is standing off to the side, watching Dean give interviews and is ushered a couple of feet away after said interview to give another interview. She wonders how he manages to keep his sanity. She’d go berserk if she’d have to repeat herself so many times. But he does it with a smile on his face. Albeit, it doesn’t look like it’s genuine. She knows that by now. 

“Well, hello beautiful,” A voice next to her makes her jump a little. 

She turns her head to look, smiles a tired smile when she sees who it is. The only guy she doesn’t have to fake it for besides Dean and Bobby.

“Hey, Sam,”

“Hey, you okay?” 

What is it with those good looking men? Why do they always seem to know when things are not o-fucking-kay?

“I’m fine,” She answers. 

“No, seriously, what did he do? Just tell me when you need his ass kicked. Hell, if I knew this morning I’d have him beat up for you.” 

She snorts out a laugh. Whatever Sam’s doing, it works.

“Nah, really, Sam. I’m just lost in thinking of how to get back on my feet when I have to move out of Dean’s penthouse.”

“Why are you thinking of moving out? We have found jack squat.”

“Good things never last, right?” She exhales and looks over to Sam. She tries to smile, but it doesn’t really come across the way she wants it to. 

Sam comes to stand before her, places his finger underneath her chin and pushes it up so she can look at him, “You feel something for him, don’t you?” 

Snorting again, she turns her face to the side, chuckling drily, “Nah,”

“Y/N, you’re transparent as a book in this library. I can read you,”

She sighs, “Even if I do. What does that change, huh? It’s not like I belong here, Sam. Look at me. My feet are hurting, I’m wearing uncomfortable underwear and my boobs are pushed up by a fake bra,” She leans in to Sam, to whisper because she doesn’t want others to hear, “Everything is fake. From the way I dress to the way we behave. I don’t know how long I can do it.”

“What do you think will happen if you tell him how you feel?” 

The laugh that’s coming out of her sounds more fake than before, but it’s genuine because the question is so absurd, “Please, as if Dean cares. He doesn’t believe in love. He’ll probably be relieved when this is all over so he can go and date super rich models and parade them around on his arm.”

“Y/N,” Sam says, his voice gets a little lower, “I’ve known Dean for quite some time, and it’s true, yeah, he doesn’t believe in love, but even though he might not be able to love you, I still think he cares because of the way he looks at you. I’ve never seen him look at anyone else like that before.” The tall man smiles down at her, “And let me tell you a secret. Dean always says he doesn’t believe in love but you wanna know the truth?”

She nods her head. 

Sam chuckles, “It’s because he doesn’t know what love feels like as he’s never been in love. Chances are that he can’t distinguish it from the other feelings. He doesn’t even know that caring for someone, wanting the best for them, thinking about them — that’s already love.”

Her cheeks get warmer. But before she can utter a word in reply to Sam’s revelations, Dean’s standing by their side.

  
  
  


_______________________________________________________

  
  
  
  


Dean’s seen them out of the corner of his eye. He was distracted by Sam. Can’t lie. Not even talking about the pang of jealousy that hit him out of nowhere. And when they lean so close to each other, he almost breaks off the interview. 

There’s something going on that he doesn’t know and it kills him. Dean hates to be out of the loop and he’d like to know what they are talking about. He also knows that it’s probably none of his business, but still...

And today started great too. Started absolutely fantastic with her kissing him awake. He didn’t want to get up, wanted to stay on that damn couch longer. Next time, Dean thinks, next time they really should get into a bed. Fact is that he’s had the best sleep again and he would have no problem if it’d become a habit. 

But then he went for a sparring session with Sam and when he came back, the ease they both woke up in was just not there anymore. There’s something troubling her, but she wouldn’t tell him and that too, is killing him. 

“Sam,” Dean greets his friend as he pushes his way to Y/N and wraps a protective arm around her waist. It’s probably more possessive than protective but who cares. “What are you doing here?”

“Yeah, about that,” Sam says and looks down to his toes, “I need to talk to you in private.”

Dean tightens his grip around her, “I think Y/N is ready to hear it too, whatever it is.” 

It’s really just his way to include her. He drove here with a heavy heart. Thinks it’s fucked up that she has to play a role by his side and be reduced to arm candy next to him when he knows that she can be so much more. There’s something about her and it’s not just the looks. He thinks she’s clever, she’s witty, she shouldn’t be reduced into being anyone’s arm candy. Not even his.

Dean feels guilty too. Guilty that they have to hide Olivia. Because today, Olivia could have easily come with them. There’s a whole wing dedicated to children's books. With a big castle and a slide. Liv would have had the time of her life.

“Right,” Sam says and clears his throat, “You’ll get the memo, but it went through me first so I’m delivering it to you hot on a silver platter.”

“Sam, will you get to the point?” Dean’s getting impatient. 

“John is holding an emergency meeting with the shareholders. He’s going to propose you marry soon or you won’t get the shares at all.”

“What?” Dean frowns. “He can’t do that!”

“I don’t know how, but he found a way to do it. Our team is looking into it as we speak. I guess they found a loophole before we did,”

“Fuck,” Dean mutters. 

“I have to go back, it’s not nice to pull my people in on a Sunday and the boss is not there. Anyway, I can come meet you later, we can discuss then,” Sam nods before he walks out of the library. 

“What now?” She asks. Dean’s still chewing on his lip.

He decides to push it aside for the time being. Pulls her into him and places a kiss on her forehead. 

“I don’t know,” He answers, mumbles into her temple. It’s a little lie. He does know. He knows what the right thing would be. The idea doesn’t seem too bad in his head. “Come on, let’s go back to Liv.”

**Notes for the Chapter:**

> Ohhhh, what idea is brewing in Dean's head? lol


	15. Chapter 15

The drive back is spent in silence. It’s deafening but Y/N doesn’t dare say a word. She doesn’t know what to say because she has no idea what’s going on in Dean’s mind. 

Dean grips the steering wheel so tight, the white of his knuckles are showing. Every now and then, he rubs at his scruff. It’s longer. He didn’t shave today. She wonders if it’s deliberate. If it’s because she said that she liked the slowly growing beard because she thinks it makes him softer. It must be itching from the way he rubs at it constantly. Is he going to grow it out for her? That would be ridiculous as he surely doesn’t take advice from someone he pays to be in a fake relationship with him.

Dean still hasn’t said a word when they arrive. He walks to the elevator absentmindedly, waits for her to join him with his hand in his pockets. As they board the elevator, he leans the back of his head against the cold wall and exhales loudly.

It’s driving her nuts because she doesn’t know if she’s the reason for him being so distant.

“Penny for your thoughts,” She asks. Her hand clutches at the railing behind her back and she looks up at him, tries to smile a little to lighten the mood that seems to have stayed way down since Sam came to the library.

His eyes widen as he looks at her, as if the question manages to pull him out of the place he’s been in without him even realizing it. 

Dean shakes his head, letting out a soft snort, his lips curve up a little, “Sorry, I was in my head,”

“I could see that,” She says, and adds, “What are you thinking about?”

“Ah, it’s nothing,”

Y/N cocks an eyebrow, stares him down. 

Chuckling, he lets out another breath. “Well, I was wondering… would it really be so bad if we’d marry?”

“What?” 

It comes out loud, a little shrill in this confined space and Dean flinches. 

“Look,” He clears his throat, “I like you, obviously. I trust you. We’re doing nothing else than extending the contract. That way you will be safe too, and Liv. You don’t have to return to your life and can stay here.”

“Dean, you obviously don’t know what you’re talking about,” She scoffs. 

It’s not like she doesn’t let his word sink in. Oh, they sank in, alright. And even though her heart says  _ yes _ , her mind doesn’t quite agree. 

“Y/N, I know what I’m talking about, okay? I’m a strategist. I know what I do and I think about all the consequences before I do anything. But this,” He pauses. She doesn’t know what for. To emphasize it? To be dramatic? She picks the second one. Dean’s so fucking dramatic. “This? I’m not scared about the outcome. I know that it’s a win-win situation, isn’t it? You can stay here, you don’t have to worry about money because I make plenty. You’re not in it for my mon—”

“—Are you hearing yourself? The money is all I’m in this for? We have a contract!” 

She can’t say that she’s not mad about it. His suggestion doesn’t sit right with her.

“You know what I mean,” He interjects.

She does know. She’s really not interested in his fortune. She thought she could make a couple of bucks to tie her over. To provide Liv with a great future. The money should go into Liv’s college fund. Should go towards a future for her child. Still, it doesn’t sound right to get married when love isn’t involved.

Dean seems to know that her thoughts drift off to her daughter and he opens his mouth to speak. It comes out softer, gentler, “Think about it, Y/N. I’m going to talk to Sam of course, but really think about it, okay? I can take care of Liv, you don’t have to work your ass off. It’s really the best, and I can’t lie. I’m happy it’s you.”

“Dean,” Her voice gets calmer, “Do you really want to marry me? Do you want to marry a single mother with a child attached? Like, it doesn’t matter if we divorce after a couple of months after you settled with your shares, but I’m going to be the first wife. _Your_ _first wife_. You’ll remember that for as long as you’re living.”

He purses his lips, and she doesn’t know if he just pretends to be thinking because she told him to.

The elevator pings to signal their arrival on the floor and she steps out, leaving Dean to trail behind her. They get into the apartment and he closes the door. 

“Right, I have promised to teach Liv how to swim. You can join us if you like?” He suggests, and she nods her head before she turns around to walk towards Liv’s room. But then his hand comes up to grip her wrist. Dean pulls her closer, leans down to whisper to her, “And you know, if we do this right, there won’t even have to be a divorce and you can stay my first and only wife.”

Dean lets her go with a heavy drumming of her heart.

  
  
  
  


*

  
  
  


She helps Liv get ready for swimming, lays out the girl’s array of bathing suits for her to choose from. It takes her awfully long to make up her mind if she wanted to wear the Frozen or Rapunzel one because she wanted to look good for the lesson. 

The little girl is so giddy about her lesson with Dean, and honestly, Y/N is surprised that Dean had promised Liv to teach her and what astounds her the most is that he kept his promise. 

Dean has no obligation whatsoever towards her or Olivia, but he’s going out of the way to clear his schedule just so he can teach Liv things and that’s good, isn’t it? Especially now that he wants her to marry him.

_ Oh god _ . The marriage talk is still not off the table. She thought she really wouldn’t have to. She thought she’d be out of here sooner than she can blink. Marriage is a big step. Even if it’s fake —  _ especially _ if it’s fake. And yeah, she told him that she’s going to always be the first wife, but it’s the same for her. Dean will always be her first husband and she will remember that. When it will really be all over, she’ll be a single divorced mother, not only single but also divorced. The thought makes her shiver because that’s about the polar opposite of what she thought her life would be when she was a young girl dreaming about getting married in white to the boy she loves.

And there’s also the problem with Jimmy. She can’t tell her ex that it’s going to be a joke anymore when they are really going to get hitched. And she has to tell Dean about it, but she really doesn’t want to.

Ugh. Since when did her life get so complicated?

  
  
  


*

  
  
  


Liv’s already in the pool with Dean when she joins them, wearing a bikini Garth had sent to the penthouse. There were a couple she could choose from and she decided on this one because some are really too revealing. 

She wears a short robe over it, though. 

The two are splashing around at the shallow end of the pool. Dean’s torso is above water and he supports Liv's stomach with the flat of his hand, letting her hover above while the child is kicking her feet about, splashing water into Dean’s face and he has to squint his eyes, but he’s laughing.

Seeing Dean like this makes her chest swell. There’s just something about the gentleness he shows Liv that makes her heart full. It’s also the first time she’s seen him naked. Well, not really naked since he’s still in his swimming trunks, but it’s the most naked she’s seen him, and boy, he definitely is a couple of leagues above her. Maybe above anybody for that matter. 

His chest is broad, his stomach well defined. There are some outlines of his abs visible, but he doesn’t look like those crazy male models who only have abs and nothing else. He’s lean and firm, not to forget, strong. His biceps are huge and what she really thinks is cute is that Dean has freckles sprayed all over his body. 

“You want to join?” 

The deep rumble of his voice tears her away from her daydream and she’s a little ashamed that there’s slick pooling between her thighs. 

“Mommy can’t swim,” Olivia says.

“She can’t?” Dean asks Liv, thinking he didn’t hear right.

“I can!” She states, “Well, you know, I can keep my head above water for ten seconds,” 

That’s a little bit exaggerated. Maybe it’s five seconds if she’s lucky. Mom never really taught her and she never really needed to swim in her life. That’s why she also can’t really teach Liv.

Dean starts to laugh before he turns his attention back to Liv, “What do you say, does your mom need swimming lessons as well?”

“Yeah!” The little girl jumps up and down and Y/N rolls her eyes. 

They enjoy the day by the pool and the maid brings out sandwiches and fruit for them to devour while they have a swimming break. 

The sun starts to set when Dean is called to see Sam. Her presence is not required, so she retreats with Liv. Bathes the girl and watches some TV with her before bedtime. 

  
  
  
  


_______________________________________________________

  
  
  
  


The afternoon out with them was distracting. He thinks it was exactly what he needed. Dean completely lost track of the time and forgot that Sam said he wanted to come over and when his friend did, Dean’s still in his trunks that have thankfully dried up already as they were just lounging around by the end of the afternoon.

It’s weird. It definitely doesn’t happen often that he forgets meetings or appointments. He guesses it’s because the two girls give him that sense of belonging, a sense of family that he never had, making him truly happy so that he forgets about everything else. Dean comes to the conclusion that he wants to hold on to that. Liv is such an adorable girl, and somehow, she grounds him. She’s quick to judge and she doesn’t fear him. To her, he’s not a scary boss. She’s so fucking witty, too. Dean is really trying hard to not make a mistake in Liv’s book. Also in her mother’s book. He’s trying hard there too, no doubt about it. 

Y/N didn’t join them in the pool, even though Dean would have loved to see her body. He’s sure she was wearing a bikini underneath that robe. But while they were lounging he could see a sliver of exposed thigh, and it’s not like he’s a teen, but that already turned him on and it made him hard. His body totally acts like he’s a teen around her.

So, when Sam comes around, Dean excused himself to go greet his friend. Has to be careful and not turn to face them because he’s sure that even if he’s only semi-hard, Y/N would have noticed it. 

He makes his way to his study and closes the door behind him. Sam’s already nursing a whiskey, sitting on the set of couches in the middle of the room. He tries to act relaxed, but the tick in his jaw gives it away. Dean knows his friend too well, knows when something throws him off. Sam’s usually very gentle and calm, the polar opposite to Dean. Maybe that’s why they work together so well. 

His friend raises an eyebrow when he sees Dean walking in in his swimming trunk. “Uh, did I interrupt?”

“Interrupt what?”

Sam’s eyes are trained on Dean’s crotch and Dean exhales loudly, feels the urge to roll his eyes to the back of his head. Instead of answering Sam, he makes his way over to the bar and pours himself a glass of whiskey. Dean walks back and sits down with a grunt. Somehow, playing with Liv the whole afternoon is more exhausting than working from sunrise to sunset. 

He takes a sip and swallows it down, relishes himself in the burning sensation of the alcohol traveling down his throat. 

A look at Sam tells him that he doesn’t have good news. 

“So,” Dean says, “Hit me,”

“Well, what can I say?”

“Oh, he’s good. He’s fucking good, isn’t he?” Dean chuckles as he shakes his head. He knows his father too well. Dean has good lawyers on his payroll, but sometimes, he thinks, his father has better ones. 

“Fact is that he found the fucking loophole, Dean. His team found out that the contract says if a shareholder is holding more than 20%, he’s allowed to make requests before he gives up his shares.”

“Yeah! I know that! But it’s for if someone says that they want to split up their shares between two holders or whatever. It’s not to request me to marry?”

“I’m afraid it’s legal since his lawyer sets up the company shareholder contract. They knew exactly what they’re doing,”

Dean rubs a hand over his face, rubs a little longer around his scruff. It’s started to itch uncomfortably. Most of the time he can ignore it, but sometimes it itches so bad he has to scratch it. But Y/N said that it makes him look softer. Maybe that’s a good thing. A change of image. Moving away from Dean Winchester, the bachelor, to Dean Winchester, a married husband with a child.

“Did you get the meeting invitation for tomorrow?” Sam asks, taking another sip from his glass.

“Yeah, but I didn’t read it.”

He really didn’t. When his phone pinged with the email, he was quick to dismiss it. Reading it would have ruined the afternoon and he needed to be in the happy headspace when he was going to spend time with his girls. Well, not exactly  _ his _ girls, but it feels like they are.

His friend chuckles, “Right, it’s tomorrow morning at 9 AM. Everyone already RSVP’d. Those who can not physically be here will dial in,”

“Great,” Dean groans. It’s really just what he needs. Spending Monday morning in a boardroom full of shareholders.

“Have you talked to Y/N?”

Inhaling sharply, Dean holds his breath for a short moment before he speaks, “Yeah. I told her to think about it.”

“Think about what?” Sam seems to be puzzled. Maybe because Dean hasn’t told him about his plans. He knew he’d forgotten something. 

“About marriage.” He says simply.

“You want to marry her?”

“Yeah,” He nods his head as if it’s no big deal. Which, to be fair, it really isn’t a big deal to him. At least not when he weighed all his other options.

“Jesus, Dean. You really want to go through with it?”

Dean toys with his index finger on the rim of his glass, “If she says yes, it’s on. We will have to amend her contract.”

“But you won’t have a prenup,” Sam says. It’s more a statement than a question.

“I don’t need a prenup if I have another contract.”

“The contract doesn’t stop her from taking a fair share if you guys divorce,” 

Sam’s being a wise ass. As if Dean doesn’t know. Dean also knows it’s a way for Sam to tell him in his own words that marrying without love and prenup is the stupidest thing to do. Dean doesn’t share Sam’s view. Not with her.

“Then I’ll give it to her,” His voice is stupidly calm. A divorce is not really on the cards. Not when it involves an innocent child. It’s not like he doesn’t like her. He does. A bit too much maybe. It’s only that he doesn’t love her and will never be able to, but does it even matter?

His friend cocks an eyebrow at him.

“She’s not like the others,” Dean mumbles.

Sam chuckles, “I know that. That’s why I’m not fighting you more. You chose wisely, but isn’t it too soon? Like, I really have a feeling that you want to force it so you can rub it in your father’s face.”

Dean shrugs. He really would love to do that. It would be great if she’d have an answer by tomorrow morning so he can cut to the chase and announce the news before his father even announces his. There’s a little smirk playing along his lips, when Dean thinks about it, “Maybe,”

“Are you going to do something stupid?” Sam raises an eyebrow.

“Nah,” Dean chuckles.

  
  
  
  


_______________________________________________________

  
  
  
  


Y/N comes out of Liv’s room after she has tucked the girl to bed and walks into the living room to gather Liv’s toys that she left lying around everywhere, when she notices the pool lights still on and Dean’s in it. He has a bottle of whiskey by the pool, and a half-empty glass sits next to it. His arms are braced on the edge of the pool as he toys with the glass. 

Slipping out, she closes the door to the terrace behind her. 

“You okay?”

Dean looks up to her, snorts out a chuckle. He’s not really okay, she can see.

“I’m fine. How’s Liv? Is she already in bed?”

“She’s exhausted from swimming and is probably already asleep,” She smirks. She takes the bottle and glass away and places them on the table by the lounger.

“Hey!” Dean shouts out.

“I don’t think you should drink when you swim, Dean,”

Dean doesn’t seem to protest any further as he has already turned around, sitting on the ledge that’s in the pool. She sits next to him on the edge, dipping her legs into the water that’s pleasantly warm. 

He turns to her then, braces his hand on the edge either side of her thighs. Looking up at her, he smiles. There’s the boyish glint in his eyes, his crinkles deepen around them. Dean’s hair is all damp, droplets of water all over his face. He looks absolutely delicious, she can’t lie about that, and her body neither, as there’s a warm feeling in her stomach when she looks at him.

“You okay?” She asks again, it’s her motherly instincts kicking in. The need to know that the people she cares for are okay.

His hand comes up to rub along her exposed thigh, wetting it with his wet hands. She bites on her bottom lip because his touch makes her feel things. 

Dean cranes his neck, places a soft peck on her lips before he nuzzles his nose along her chin. 

“I am now,” He whispers. 

It makes her insides flutter.

She lays her hands on his and they both look down at their hands. She turns his hands around, sees the pad of his fingers and his palm wrinkling from the water. She wonders how long he’s been in there.

“C’mon, maybe you should get out,” She proceeds to stand up, breaking their moment. 

He looks up at her, frowning a little, but then he chuckles and holding out a hand for her to take, “You’ve got to help me out,”

Gripping his hand in hers, she wraps her other hand around Dean’s wrist just to make sure that she can pull him up. She pulls and pulls, but he won’t budge. Instead, Dean laughs. 

Before Y/N knows it, Dean pulls. Hard. She lands in the pool and immediately the sense of panic rises. Her head is below water and she tries to push to the surface, but she doesn’t know up from down. The world has suddenly gone silent, there’s no sound coming through to her ear. She wants to breathe, but her mouth fills with water. She wants to call out, but all that comes out are bubbles.

Suddenly, a strong arm wraps around her middle, pulls her up to the surface and there’s another arm that wraps itself around her body, hand resting on the nape of her neck as she’s pulled into an embrace. She coughs and sputters out water, her whole body trembling.

“‘M sorry,” Dean whispers, stroking a hand over her head while his grip tightens around her body, “I forgot you can’t swim,”

Her face rests above his naked shoulder, her chest heaves because she’s trying to catch her breath while still coughing. 

“I got you,” Dean’s voice sounds distant, but soothing nonetheless. “I got you, Y/N.”

“Yeah,” She nods because she knows. 

“I got you,” Dean whispers, like a broken record. And then, “I'm sorry,”

It’s not his fault. It’s a stupid joke. He didn’t know, didn’t think. It happens.

He walks the two steps to the ledge in the water, sets her on it, stands in front of her and cups her face between his palms. His thumb strokes along her wet face and he’s looking at her with a frown etched deep between his brows, like he’s really worried. “You okay?”

The words won’t come out, so she nods. 

His lips find her skin, kisses her forehead, down to her nose, and place kisses on her eyelids. His scruff tickles her cheek and she has to grin. The moment of panic and shock, gone. 

Dean exhales what she thinks is out of relief and when she looks up, his lips curve up too. The frown is almost gone.

“I’m sorry, I didn’t mean to. Fuck, I’m an idiot! It’s just a joke and I—”

“—Dean?” 

“Yeah?”

He’s still riled up. It’s totally cute. 

“Can you shut up and kiss me?” Y/N asks with a playful glint in her eyes and honestly, it’s super bold of her to ask, but it’s something she needs right now and she doesn’t even know why.

“God, yes,” Dean sighs out relief, smirks a little too as his hands are cupping her face and he leans closer and down, pressing his lips to hers gently.

Breathing gets harder when he kisses her like that and even though the kiss almost cuts off her air supply, she still wants more. Her hand wraps around his neck as she teases her tongue along his bottom lip. Dean parts his lips slightly at the feel, letting her slide her tongue into his mouth as his one hand travels down along the column of her throat to her chest.

Dean tastes of whiskey. His kisses are always bittersweet, and she likes that, feels the alcohol on her tongue, feels it in her bloodstream even if it’s not possible. She gets drunk on his kisses and she figures. If she could get drunk on something, it’s definitely Dean.

He skims the nail of his index finger down her front, leaving goosebumps on her skin in its wake. Dean stops at the knot that is still holding her robe together, pulls on it and opens it up. The material is clinging to her upper body, and he quickly helps take it off, parting from her lips to be able to do it. 

His one hand goes to her hips, big palms touch and squeeze at her flesh as Dean claims her mouth again, kissing her harder and deeper than before, fucks her mouth with his tongue hungrily. She likes that too, likes the force of him on her, the way he kisses her like she’s the air that he needs. His finger toys along her bikini bottom before they dip inside the front, only teasing.

Y/N moans into his mouth, nibbles at his bottom lip as she wriggles with her hips, tries to get him to touch her where she’s desperate to be touched right now. She’s needy. A trait she just picked up since she met him.

Dean chuckles into the kiss, “What do you want, Y/N, huh?”

“You know,” She whispers back. He fucking knows.

“I’d like to hear you say it,” He says cockily, his other hand leaves her face, goes straight to her nipple that pokes through the fabric of her bikini top. He pinches at it, making her arch her back at the feel and inhaling sharply. Dean chuckles some more, pushes the cup of her bikini out of the way to squeeze her tit in his hand before he pinches her nipple again, pulls at it too, “Say it, baby,”

His voice is smooth like honey, yet, it cuts through the thread of inhibition that she’s holding on to.

He dips his head lower, nibbles along her jawline, goes down to her throat and sucks sharply at a patch of skin. It makes her squeal, makes her pussy throb, makes it clench around nothing.

_ God _ , she wants him so bad.

“Want your fingers,” She breathes out. She opts for the fingers because she knows that he won’t fuck her. 

Dean chuckles, licks at her skin from her chin to her ear, “Yeah? My fingers, huh?”

“Yeah,” Her hands grip around his biceps, feeling his muscles moving as the fingers of his hand go lower inside her bikini bottom, until he rubs the pad of them against her clit.

Y/N leans back some more, giving him better access. She’s shivering, but it’s not from the cold of the water. 

He cups her whole cunt in his palm, the tip of his fingers reaching almost to her asshole and he growls next to her ear at the slick he feels. She’s slippery wet and it’s definitely not water. 

Dean continues to nuzzle his nose against her temple as he toys at her entrance, dips his finger in just a little. It’s not nearly enough. He’s a fucking tease and she has the feeling that he knows it.

“Fuck,” He growls. 

She anticipates that finger inside, wriggles around and pushes her hips up, wants to make him sink that finger into her needy cunt but instead of pushing it in, Dean suddenly takes it away. 

It happens so fast. 

Both his hands go underneath her ass, lifts her up and places her on the edge of the pool. She feels a hand curl on the back of her neck, pulling her down to kiss him while his other hand trails along her thigh from her knees to her center. 

Dean’s finger strokes along her slit, and he groans into her mouth. He breaks the kiss with a sharp tug, sinks his teeth in, making it hurt. He leaves his forehead on hers.

“I wanna taste you so bad, Y/N, can I?” His voice is deep, low, barely a whisper.

Taste her? Like, going down on her? Fuck, it makes her pussy clench thinking about it. It has been years since that happened. 

She nods her head, her lips pulled between her teeth soothing the pain Dean inflicted.

“You’ll let me taste you, yeah?”

_ God _ , the way he says it turns her on. She nods again.

“I want you to say it, sweetheart,”

Fuck. Voicing what she wants is such a big step for her. But she’s desperate, so she bites on the inside of her cheeks before she nods again and pushes “Yes, please,” past her lips.

“Good girl,” Dean coos. His hand goes from the back of her neck to the front, squeezes her breast and toys his finger around her nipple. He kisses his way down her throat and she arches her back, giving him better access, his longer scuff scratches her skin pleasantly. 

Dean seals his mouth around her nipple, sucks the hard nub in sharply only to let it out with a lewd pop. Letting out a deep growl, he moves over to her other tit, twirls his tongue around her other nipple before he sucks at the swell of her breast. He sucks so long and hard, she’s sure he’s going to leave a mark. 

Her hands are in his hair, nails digging into his scalp. “Dean,”

“I know,” He mumbles as he kisses his way further down her torso, past stretch marks and things she keeps hidden from anyone in the past years, “I got you,”

She leans back, her hands braced on the concrete as she watches him work his way down. 

Dean’s hand grips around her thighs, pulls her ass to the edge of the pool. He pushes her bottom out of the way, threads his finger through her slit, from her clit to her entrance. His gaze is fixed right there and she feels a little uneasy.

He swallows thickly, “Such a pretty pussy, baby,” 

Y/N feels her cheeks flush more than before. She can’t recall someone telling her that. She also doesn’t really believe it, even if Dean makes it sound so believable.

Dean looks at her as if he’s asking for permission. As if he wants to make sure that it’s really okay. 

She nods, her lips tugged between her teeth, anticipating it so much.

Nodding back, she notices a crooked grin spreading on Dean’s face, and she bites harder on her lips when he ducks his head down. 

He places his hands on her knees, spreads her some more and she should be ashamed as she’s completely exposed, but she can’t even think of it too long because his tongue swipes up her slick cunt, making her jerk but his hands are holding her in place. 

“Fuck,” She curses and drops her head back. 

His tongue is massive and he groans out as he licks along her slit up to her clit, seals his mouth around it to worry at her hardened nub. Her one hand goes to his head, fingers threading through his short hair. 

He hums as he sucks and licks at her folds, and his scruff rubs at the inner of her thighs when he turns his head just right. She’s sure there’s going to be beard burns. Not that she cares because Dean’s licking around her entrance, making her forget about everything else. He dips his massive tongue inside her pussy, and god, his tongue is long and huge, it elicits squeals and laughs from her.

“Oh god,” She breathes out and she’s smiling because it feels too fucking good. 

Nobody had made her feel like this before. Jimmy went down on her twice, but it just seems like a chore for him, and he probably only did it because she wasn’t wet enough. With Dean, it’s totally different. He isn’t doing it to get anything out of it and to be honest, she’s always been plenty wet for him. 

Dean makes out with her pussy. He’s eating her out like the man he is, dominant and demanding with an underlying finesse and softness. He hums and growls as if it’s really good, it blows her mind. Dean makes slurping sounds too and she gets a little flustered at that, it sounds obscene. 

God, his tongue is fucking talented, she wonders if there’s anything Dean can’t do. 

His one hand leaves her knee, skims up her thigh and then he toys at her entrance with the tip of his middle finger. She yelps up when he slides it inside. He’s still sucking at her clit, groans too as he begins to fuck his finger in and out of her. When he adds another of his fingers, she feels so fucking full and he curves them too, hitting a spot she never knew existed.

“Fuck,” Y/N moans.

Her nails are now literally digging into his scalp and she feels the orgasm coiling inside of her. 

It’s embarrassing how quick he can make her come. Whereas when she’s doing it herself, it can take her up to an hour or even longer.

“Shit, Dean,” She keens out his name, feels her thighs trembling and her toes curling. The sensation winds up inside of her, and it’s just a matter of seconds until it snaps.

“Come,” He growls, looking up from between her thighs, “You can come, baby,”

_ Fuck. _

Her fingers fist his hair now and she wriggles her hips, trying to get him to fuck his fingers deeper into her, trying to get him to suck at her clit harder. Dean lets her. He fucking lets her. What does that say about him?

“Oh god, don’t stop, don’t stop,” She whines, might even sound needy, but that’s because she fucking is.

He doesn’t stop. Instead, Dean starts to hum and her clit starts to vibrate.

_ Shit. _

Y/N’s shaking all over, her thighs squeeze together, her pussy squeezes around his digits and she throws her head back, closing her eyes as she squeals out in delight.

  
  
  


_______________________________________________________

  
  
  


Dean’s head is locked between her thighs, his fingers are gripped by the impossibly tight clench of her cunt and he feels her cum soaking his chin. He can’t really breathe right, but it’s not like he needs air right now. 

He places kitten licks over her clit, kisses it softly and she’s jerking underneath him as she comes down from her high. 

_God_ , the sounds she made when she comes. A squeal of delight, it’s something else. He doesn’t think anyone he’s met is having so much fun coming as she does. It makes him harder than he cares to admit, makes him want to hear it all the time.

When the time comes and her legs and pussy releases him, Dean pulls his fingers out, licks at her entrance some more, drinks in the heady taste of her that he thinks he can’t get enough of. 

He’s been good, fucking good actually, because it needs everything in him not to just whip his hard dick out and sink into her still pulsing cunt. He’d love to do that, of course he would. It’s just — he can’t. But also he doesn't know how long he can keep it up. Not when she’s so fucking good for him.

When Y/N calms down enough, Dean hears giggling above and the hand that’s in his hair tugs a little sharper, pulls him up. He can’t say he doesn’t like it.

“Good?” He asks smugly, he knows that he’s not really bad at it. He also likes doing it and that’s probably why. It has something to do with his oral fixation, Sam once said. Not that Sam knows every detail about Dean but girls apparently talk. A lot.

“Fuck yes,” She’s laughing and Dean moves up, nuzzles his nose against hers. Her hand cradles his face that’s all wet and it’s not from the water. 

He kisses her, lets her taste herself off the tip of his tongue, “You taste so fucking good. I should take my time next time,”

It blurts out of him by saying next time. He hopes there’s going to be a next time because now that he’s tasted from her source, he doesn’t think he can stop.

Their foreheads are still touching as he releases her bottom lip with a pop, dives in again to steal a peck.

“Now you,” She grins and it’s said with an easiness in her voice and a mischievous glint in her eyes that makes him feel things he shouldn’t. 

Dean chuckles, “Nah,”

“No?” 

He can see the pout forming, leans in to nibble at her lip, “No,” 

It’s all a farce. He would love her to. Would love to feel her hand, her mouth, her pussy around this throbbing cock. It’s just — he’s sure that if it so much as come in contact with her, he’s going to come instantly, and that’s an embarrassment he can’t face. Not when he’s trying so hard to be the one in control.

Moving in to peck her lip one last time, he retreats, dives further into the pool. It physically pains him, his cock too, to do that. 

“You should go in,” He says from a safe distance, “I’ll be out soon, I promise.”

She stands up wordlessly and he watches as her hand rights her bikini. His dick stirs again, longing to be touched. With a last glance back, she opens the door and disappears inside and Dean lets himself sink into his pool, letting the cool water ease the burning desire in his body.

  
  
  


*

  
  


Dean walks out of the shower in his underwear with his body still damp and hair wet. He had jerked himself off to the images of her in front of his eyes and the lingering taste of her on his tongue, came sooner than he thought he would. It's embarrassing, not to say pathetic even. He almost didn’t want to drink or brush his teeth because he would have loved to be reminded of her taste, but his common sense won. 

He switches off the light on his way out, wonders if he should pull a shirt over, if he should wear pants. Wonders, if she’ll be in his study, waiting for him. That’s probably wishful thinking on his part. 

While he stands in front of his dresser, debating on slipping something over his head or just going to bed and trying to fall asleep on his own, someone knocks at his door. 

His heart races as he looks over to the door. He knows who it is. It can only be one person. 

Quickly, he abandons his task, there’s no time to grab a shirt, she’d have to wait too long and maybe she’ll be gone when he opens the door. He really doesn’t want her to change her mind.

The door opens to Y/N wearing a simple white t-shirt that’s too big for her frame. There’s a tightness in his stomach and Dean pushes it out of his mind, tries not to get wound up because of a simple shirt that might or might not have belonged to another man in her life. 

Her face is flushed, something tells him that she was not prepared for him to open up the door. 

Dean wants to say something but there’s nothing coming out so he stands there, waiting for her to talk first.

She looks him up and down, her gaze lingers a fraction too long on his crotch. Dean smirks to himself. He does know that he’s not exactly bad looking. He knows what effect he has on people, especially on women, but her reaction is just too cute. Feels a little proud too. Maybe also because he knows that she is not impressed easily. 

There’s silence as she stares and her tongue comes out subconsciously, wetting her lips. He feels a little exposed, even if he’s still wearing underwear, but her gaze tells him that she would love to try to eat him alive. The gaze is not implying that she can, but it says that she’s determined to try. It’s a gaze similar to his. One he knows he shows too often when he looks at her. It doesn’t help that his dick starts to stir and he really doesn’t want her to see how much she affects him. 

“Is there a reason you’re here, Y/N?” He cocks an eyebrow in question after an agonizingly long period of silence.

It helps to snap her mind right back.

“Uh, yeah,” She looks at his face now.

“Yes?” 

He waits with bated breath.

She nods her head, “I wonder if, you know,”

Dean knows and he wants to smile, but he’s doing his best to swallow it down. Thinks that she’s going to leave once he smiles like a goddamn fucking idiot. 

He opens the door wider, “Do you, I mean,” He looks over to his made bed, “Do you maybe want to come in?”

“Yes,”

“Come on,” Dean holds out a hand for her to take, closes the door once she’s inside and leads her over to his bed. 

They somehow don’t need words to communicate.

Once she settles in, he climbs in after her, spoons her from behind, holds her close. It’s crazy how she became a fixture in his nightly routine. It quickly becomes something he doesn’t want to give up. 

He inhales the smell of her shampoo. It’s something refreshing, it reminds him of the sea breeze. Her body wash has its own scent. Coconut and honey. He could eat her up. 

“‘M sorry,” She says, and she’s playing with his hand that’s around her stomach. 

“For what?” Dean mumbles into the back of her neck. He almost fell asleep just inhaling her scent. It stupid how much it calms him but when she speaks, he jerks up a little.

“For barging in here. I just didn’t want to be alone,” Her voice is barely a whisper. He has to strain to hear it. 

Dean places a kiss on the junction where her shoulder meets her neck, where the neckline of her shirt has ridden down. His scruff scratches loudly against her skin, “That’s okay, I would have told you if it wasn’t.”

“‘K,” Y/N says and pats his hand. 

He nuzzles his face back against the pillow, presses it into the back of her neck, “Have you thought about the marriage?”

“All the time,”

“And?”

He really doesn’t want to pressure her, but also he does. Time’s kind of running out.

“I can’t give you an answer yet, Dean,”

“K,” He mumbles softly. 

“Soon,” She assures him, but her voice gets smaller. 

It’s only a matter of minutes until they fall asleep.

**Notes for the Chapter:**

> Two idiots, am I right?


	16. Chapter 16

Y/N wakes up to an alarm she doesn't recall having set. It’s not exactly loud, but it’s unfamiliar. It’s not the tone that she uses as an alarm on her phone. Her eyes fly open immediately.

It takes her a moment to realize that she’s not in her bed. Takes her a while to realize that she was the one who came knocking at Dean’s door, hoping he’d let her sleep with him because she went to the library in the hopes that he’d be there. Her heart sank when he wasn’t, and before she could even think about what to do next, her feet took her to Dean’s room on their own.

The man next to her blindly reaches out, searches for the alarm, pushes a button for it to shut up before his arm comes back around her.

It’s _ easy _ , she thinks, waking up next to him. It’s something that became familiar. Something she doesn’t really want to miss anymore, but she can’t say it aloud. She doesn’t want to jinx it.

“‘M sorry,” He mumbles, his voice is deep, husky and sleep drunk. It sounds super sexy. Dean buries his face in her shoulder, rubs his scruff on there too, “You can stay but I gotta get up,”

“What time is it?” She mumbles back, “Wait, it’s still dark, I’m not sure I do really wanna know,”

He chuckles, “5.30 AM,”

“Jesus,” She buries her face in the pillow with a groan, “Do you always get up so early?”

“I like to have time in the mornings, checking stock markets and preparing myself mentally for the day. I mostly do it in bed, so,” He rolls away from her and gets out of bed, proceeds to walk to the bathroom. 

“Wait,” She calls out and he stalls by the door, turning back to her and raises his eyebrows. Propping herself up on her elbows, she yawns, “I need to pee before you do whatever you do in there in the mornings.”

Dean groans out playfully and walks back to the bed, crawls inside and pulls the comforter over himself. 

After a solid minute, Y/N still hasn’t moved a muscle. His bed’s just too comfortable and it’s way too early to be getting out. Maybe, she thinks, the reason for her hesitation is also because of the man next to her.

Dean lifts his head to look at her, “Are you going or..?”

“It’s not fair that you came back to bed, honestly,” She lets out a groan and hesitantly rolls herself out of bed to make her way over to the bathroom, still sleep drunk and on wobbly feet. Dean chuckles as he watches her. 

“There are face cloths next to the sink and new toothbrushes in the cabinet,” He calls after her. 

Dean’s bathroom is big. Bigger than hers. It has a huge ass bathtub she’s certain he never uses. At least he doesn’t look like he has the time to spend in a relaxing bath. The shower’s all fancy with a lot of buttons. The one in her room is simpler. The bathroom is also kind of empty. There aren't a lot of things standing around. At least nothing that really indicates that this bathroom is used by someone at all. The only thing that reminds her of Dean in here is the lingering scent of his cologne that hangs in the air.

She washes her hands and takes the cloth from the rack to clean her face. She would have to wait until she gets to her room to apply moisturizer, as she’s not sure where Dean keeps his. Not even sure if he needs it, which really wouldn’t be fair if he doesn’t need anything at all. It would show that God really does have favorites and Dean Winchester would be right at the top of that list.

Taking a toothbrush out of the cabinet, she brushes her teeth. She doesn’t know where to put it after, so she just lays it next to the sink.

Dean’s still in bed when she walks out, and she slips back under the covers. 

“It’s your turn,” Y/N says and she can tell that he doesn’t want to leave the bed either. Instead of getting up, he rolls closer to her, wraps his arms around her to pull her against his body.

“I don’t wanna,”

“Mr. CEO of a multi-billion company doesn’t want to get up and earn more millions? Do you wanna risk being late? Your employees will give you a new nickname.” 

He groans, “Fine, I’m going, but you’re staying here,”

“Yes, sir,”

Dean turns his head as he walks to the bathroom, lowers his chin, and raises his eyebrows, “Is that what you like, huh? Calling me sir?”

“Oh god,” Groaning, she pulls the covers over her head, ignoring his laughter as he closes the bathroom door.

A couple of minutes later, she hears the shower.

After Dean disappeared for about ten minutes there’s a knock at the door and she opens up to Missouri. The woman is carrying a cup of coffee. She guesses that’s the first thing the woman has to do once she shows up at 6 AM.

“Oh,” The woman says, “I didn’t know,” 

“That’s okay, Missouri,” 

A big grin spreads on the woman’s face. “I’m bringing him his coffee, but I’ll go get one for you too,”

“Oh, you really don’t have to,”

“It’s my pleasure!” Missouri’s already gone and leaves her standing there with Dean’s coffee in hand. She places it on the nightstand and crawls back to bed.

When Dean walks out two minutes later, he notices the coffee, and Y/N thought he would freak out, but he just walks to the bed in only his underwear, which is totally not fair to be looking so yummy in the morning, and takes a sip out of his cup. 

He turns to her, “You want one?” 

“Missouri’s apparently already jetted to the kitchen to fetch me one, even if I told her that she didn’t have to.”

Dean chuckles. 

The next time there’s a knock, Dean opens up and lets Missouri bring in the coffee. There’s still a big grin on the woman’s face when she spots Y/N in Dean’s bed, and Y/N’s feels her cheeks heating up. 

He sits in bed with his back against the headboard, thumbing through his phone while he switches on the TV with stock market news on mute. He’s sitting there in his goddamn underwear, not even bothering to pull up the covers or anything. 

She’s watching him out of the corner of her eye and it might have been a fraction too long because Dean abandons his phone and cocks his head to the side.

He raises his eyebrows and there’s a grin playing along his lips when he speaks, “Something bothering you, sweetheart?”

Y/N sighs. 

Dean chuckles, “What is it?”

“Don’t you want to get dressed or something?”

His grin grows wide, it’s a little crooked too, “Why? Does it bother you that I’m sitting in my underwear in my own bed?”

“It throws me off,” She pouts.

“What?”

“Yeah, like, you look really good, but you probably know that already. And I’m meh,”

Dean almost snorts out the coffee that’s in his mouth, has to cough as he sets the cup down on his nightstand. 

“Meh?” He asks, and then he reaches over, pulls her into his lap with his strong arms, places her on top of him so she’s straddling him. Y/N’s not sure if he can feel how damp her panties are, but she can definitely feel his bulge, “If you were  _ meh _ to me I wouldn’t have asked you to be my fake fiancé.” Her hands are braced on his shoulder as he tucks her hair back behind her ears before he speaks again. “You know, being fake engaged to you comes with perks. Kissing you is one of many.”

It baffles her that he can say those things with a straight face. Hers is totally flushed.

“Yeah?”

“Yeah,” Dean smirks, “I like your kisses. Especially when you kiss me when I’m not expecting it. Sweeps me right off my fe—”

She doesn’t let him finish, kisses him hard and hungry as she feels. Her tongue invades his mouth and Dean gives in, his tongue fights with hers, his one hand at the back of her head, fists in her hair as he pulls her closer. His other hand is on her hips because she starts to grind on his bulge that is getting bigger. The hand on her hip is not stopping her, though. Instead, he helps in guiding her.

Breaking the kiss for a second, she pants and speaks as soon as she catches her breath, “Like this?”

“Like this,” He confirms and this time, it’s him who kisses her. 

It’s open-mouthed and messy, pent up sexual tension that’s hanging between them for days that makes them feel like this. 

He groans as she grinds on his clothed cock. The hand on her hips goes to her face and he cups it before he breaks the kiss. Dean leaves his forehead on hers and she’s still moving, still grinding. It feels too good to stop.

“Fuck, you even soaked my underwear,” He growls, “You’re such a needy girl, aren’t you?”

“God, yes,” She moans out shamelessly. It’s because she fucking is. Never knew she could be like that before she met him.

“Can you make yourself come like that, huh? Come without me even fucking you?” 

They aren’t fucking, but it feels a lot like it because his cock is hard and throbbing and it gives her just the right kind of friction. Also, Dean Winchester is fucking big. This is the closest she’s seen or felt it and goddamn, she doesn’t know if it’ll fit should he change his mind along the way and finally fucks her with his cock instead of with his tongue or fingers. God knows she’d let him. 

What tips her over is when he sneaks his hand underneath her shirt, and plays with her tits, his fingers pinching at her hard nipple. 

“Love feeling your tits in my hand,” He jiggles them for emphasis before lifting up her shirt, letting his teeth graze over the swell of her breast, leaning in to suck her nipples into his mouth.

It makes her shiver, makes her cunt throb. Dean tugs at them sharply with his teeth, sending the tingly sensation right to her core.

“Looking so good grinding on my cock, baby,” Dean’s voice is raspy, it strains a little. 

“Fuck, I’m already close,” 

“Yeah?”

“Yeah, fuck—”

“So good, fuck, Y/N. Do it.” Dean says, “Take what you need. Come, baby, come while you ride me,”

Instead of playing with her tits some more, he wraps his arms around her, pulls her close as he buries his face into the crook of her neck. He lets out a low grunt as he sucks at her pulse point, tipping her over the edge when he pulls her down harder. Her whole body shakes when she comes with a squeal.

Dean’s still holding her, sucks at her skin some more, she’s sure he’s leaving another mark apart from the one on the swell of her breast.

“Wow,” He breathes out and sprays kisses along her exposed shoulder. His scruff tickles her, “That’s embarrassing,”

Only now does she realize that he came in his underwear. 

He chuckles as he pulls her in for a peck on her nose, “Last time that happened was when I was a teenager.”

  
  
  


_______________________________________________________

  
  
  
  


It’s 8.45 AM and Dean’s sitting in his office with his chair turned to look out of the window. The skyline is vibrant. The city’s alive and thriving.

He’s thinking about something and that something’s for sure not the damn meeting. Tries to think about anything else  _ but _ the impending doom. By now, the shareholders have probably arrived and are being accompanied up to this floor.

No, he doesn’t want to think about that. Instead, his mind goes back to last night. Goes back to her coming on his tongue, wetting his fucking face. Dean thinks about her coming around his fingers, too. The taste of her is branded in his mind. When he concentrates hard enough, he can still taste her tang on the tip of his tongue. And it makes him want to go back and get another taste. He seems to be insatiable now that he knows how sweet it is to him.

Dean thinks about this morning. Thinks of how she ground on his hard cock, how she made herself come from dry humping him, how she made him fucking come in his goddamn underwear.

His dick stirs when he thinks back and that’s how he knows that he has to change the subject of his thoughts back to the meeting. He can’t possibly walk in there with a boner. Or maybe he can. Maybe he should. Out of spite. So that his father can see that nothing is fucking fake, even though she still hasn’t agreed to marry him.

He thinks back to how he left her over an hour ago with heavy limbs but happy and with a mischievous glint in her eyes. It almost made him crawl back in there. Leaving for work has never been this hard.

On his way out of the penthouse, Olivia tiptoed her way out of her room. The girl was surprised to see him, but she was on him right away, climbing up his body, not minding that he was wearing a freshly pressed suit. And she demanded that he spins her around. Of course Dean did. It was refreshing to hear a child’s giggles so early in the morning. 

She asked if it’s time to go wake up her mom, and he said that Y/N needs to sleep a little longer. He didn’t really know how much Y/N has told her child about what they are — or what they aren’t, so he didn’t want to spoil anything. Olivia then said it was okay and that she’ll go get a glass of water and will play in her room until mommy wakes up. Dean felt bad, wanted to tell the kid to go see her mom in his room but again, he didn’t know if he was allowed. But he guessed that Y/N will get up any minute now anyway. 

A knock at his office door pulls Dean back to reality.

Dean turns around in his chair, ready to bark at whoever is standing outside, but before he can do that, the door opens to Sam. 

Of course Sam wouldn’t wait for him to tell him to come in. Sam never had. It’s really a bad habit. It’s also one that’s not likely to change, knowing his friend.

“You ready?”

Dean leans his head against the headrest on his office chair. He never knew why office chairs have to have a headrest but now he’s thankful to have a chair that comes with one. He cocks his head to the side, frowns when he speaks, “No?”

“Great,” Sam smiles as he walks in further, “Did she give you an answer?”

“No?” Dean’s eyebrows knit together. “Is this an interrogation?”

His friend chuckles as he sits down and drops his laptop case next to him. “Have you told her about the meeting today?” 

“Well she knew from the way you barged into the library, but she doesn’t know it’s now, I guess. What does it matter?”

Sam shrugs as he takes out his phone and thumbs over it. “Just asking. Don’t shoot the messenger, Dean,”

Dean’s hand goes to his scruff, scratches at it noisily. He probably scratches too long because Sam tears his attention away from his phone to send Dean a glare. 

“You forgot to shave or?”

“Nah,” Dean shakes his head, “Wanna grow it out,”

“Why?”

He sighs, “Let me ask again, is this an interrogation?”

His friend looks away, occupies himself with his phone and the silence is driving Dean nuts. He figures it is too early for a drink. 

“What time is it?” He asks after a while.

“Uh, 8.51 AM.”

Dean lets out a groan.

  
  
  
  


*

  
  
  
  


“Ladies and Gentlemen,” Dean addresses the shareholders sitting in his boardroom. There aren’t many who showed up in person, a dozen to be exact. The rest dialed in via video call and their faces are displayed on the big screen, “As you all know, my father has sent out an invitation because he has an amendment to make. Specifically, a request,” Dean nods to his father and the old man nods back.

While Dean’s mind races on what to say or do next, the door to the meeting room opens and Sam slips in with Y/N in tow. They stand back, off to the side of the door. He wonders why she’s here. She’s dressed down, in black jeans and a blouse, standing tall on her heels, and she’s wearing the necklace he gave her and the engagement ring is on her finger. It has been on her finger since he slipped it on, he’s noticed it.

Their eyes meet and she nods at him with a big grin. Dean replicates it. He knows what she wants to tell him with that big grin. Sam winks at him too, but Dean doesn’t really take notice because she shines in the room and he just feels relief washing over him.

“But we will get to that later. Sorry Dad, but I have something to say too,” He states and his father’s eyes go wide.

Dean walks to the back and takes her hand, “You sure?” He whispers into her ear so only she can hear him.

Y/N nods and then she cradles his face with both her hands and pulls him into a kiss.

_ Jesus _ , he wasn’t lying when he told her that he loves her unexpected kisses. It always manages to sweep him off his goddamn feet.

“Yes,” She breathes against his lip and Dean can not hide his joy. 

He nods at her one last time before he turns to face the room, grins crookedly at the people who are staring at them.

Dean clears his throat before he speaks with a big satisfactory smile. His arm is tight around her waist, pulling her closer to him, “I’m gonna get married to this wonderful woman,” 

There are several gasps and some even clap, but his father’s expression stays stone cold. The old man reacts just the way Dean thought he would.

When the initial shock dies down, his father stands up from his chair, slow clapping for the dramatic undertone. All eyes are on his dad.

“Bravo!” John shouts. “Congratulations!”

Dean presses his lips into a thin line. He has the feeling that he needs to brace himself for whatever comes next. 

Oh, there’s going to be something coming, alright. His dad is always good for surprises. He hates it.

“That’s actually why I summoned this emergency meeting,” His father says and looks into the eyes of the shareholders who are present. Basically anywhere but at Dean. “I am ready to sign my shares over when my son has finally found someone good enough to marry. It’s also a condition my late wife put into her will because she wanted to see Dean happy,”

His father pauses and finally, he looks at Dean. “I’m delighted to hear that he has now finally found someone who could persuade him to settle down. Kudos to you, Y/N,” His father sends her a nod.

Dean doesn’t like that. Doesn’t like how her name rolls off his father’s lips. It doesn’t sound right. 

John goes on, “Well, now that my wish is halfway there to completion,”

“Halfway?” It blurts out of Sam and Dean simultaneously.

“Yeah,” His father says, “My other condition is that you marry this coming Sunday,”

There are the gasps again. Louder this time.

“What?” Dean shouts out.

“Did I stutter?” John cocks an eyebrow, a smug grin widens on his normally stern face. “Marry on Sunday and you’ll have my shares on Monday.”

  
  



	17. Chapter 17

Y/N’s jaw drops. 

_ What?  _

_ Oh no.  _

_ No no no no no. _

_ Sunday?  _

That’s in like… her mind pauses mid-processing to count the days in her head… She uses her fingers, just to be absolutely sure because she doesn’t really trust her brain right now. But she does it subtly, her fingers drumming against her thigh to count the days.

Six days. 

No matter how many times she counts it, it’s six days. 

Sunday’s already in six fucking days! There’s not enough time to get accustomed to getting married, not to say that it’s too short to get accustomed to the  _ idea  _ of marriage! She has to tell Liv and speak to Bobby, and oh god, this is going to end in a disaster, she just fucking knows!

Dean’s grip tightens around her waist, fingers digging into her flesh just a tad too deep. He’s still processing the news too, as everyone in the room is. She glances up at him, sees his jaw ticking, sees him swallowing the realization, his lips pressed into a thin line. 

Mr. Winchester Sr sends a knowing look into the round of shareholders, grinning smugly as he does. She can see now where Dean got that grin from. John opens that stupid mouth of his to speak, “I hope you are all free to attend on Sunday.” 

_ Oh no _ , they’re all going to attend? It’s ridiculous. His son is getting hitched and John invites people on Dean’s behalf. If it was up to her none of them would be there. Most likely not even John. But she has no say in this and she knows how important it is for Dean, and honestly, she’s paid to play along and not because he wants her opinions on things that should definitely not be of her concern even if she’s an important piece to this game.

Y/N can’t imagine that Dean’s happy about it either, though, if the grip he has on her is anything to go by. His fingers digging into the flesh of her waist as he pulls her even closer, as if he’s holding on to her so as not to lash out at his father. When she looks up at him, his jaw is still ticking.

  
  
  
  


*

  
  
  
  


The meeting was pretty much over after that and Dean ushered her into his office afterward. His fingers curl into the side of her waist, still holding her so tight that she’s absolutely sure that he’ll leave a bruise. Walking swiftly along the hallway, they ignored all the other people and Dean even shoved at some who were in the way. It was hard for her to keep up; it was even hard for Sam and that’s saying something.

“Fuck,” Dean mutters under his breath as they are safe and tucked away from John in his spacious office. He even locked the door, but he is seemingly aware that he can’t be too loud in case people are walking past his office. Dean threads his hand through his hair, scratches at his scruff as he walks deeper into the room.

Striding over to his mini bar, he takes the bottle of whiskey and pours it into the tumbler sitting next to the bottle. Y/N’s quick to be by his side, taking the tumbler right from under his nose as he finishes pouring two fingers full of liquor and lifts it up to her lips to drain it in one go. 

God, she needed it. The liquid burns its way down her throat. It’s unfamiliar and she’s definitely not used to drinking hard liquor, only tasted it from Dean’s lips so far, so she squints and coughs after to shake the burn.

When she looks up again, he’s still holding the bottle in his hand, frowning at her. But it’s not malicious. She can see the playful smirk hiding behind his tightly pressed lips. 

“You want another?” He asks as his frown makes way to a grin. It’s crooked, totally playful, the tip of his white fangs showing.

“I’m good,” She sputters out hoarsely, still trying to find her voice after swallowing it all in one go, “Thanks,”

“You make me all tingly when you act like that,” Dean chuckles and takes the glass from her hand. He uses it to pour more into it for himself, drowning it all without even making a face.

“So, damage control,” Sam announces from where he’s sitting on the couch, his laptop propped on his lap, fingers effortlessly dancing over the keyboard.

“I think we can all agree that the damage has already been done,” Dean grumbles. His hand finds her shoulder and he walks along with her to the window, leaving his friend to type up something on his laptop. He leans down to her a little. She can feel the whiskey on his breath and even though she didn’t exactly enjoy the liquor, she somehow craves more, “You really okay with that, right? I promise, I’ll make it worth your while,” He says, his voice soft.

“It’s okay, I just... I didn’t think it would be this fast. I have to tell Liv, and Bobby and I don’t even have a bridesmaid. Do I need one?” 

It blurts out of her because fuck, she’s never been married before and she doesn’t know the etiquette. It’s not a normal marriage either, it’s one with stinky rich people and they usually expect something nice, no?

“Honestly, it’s up to you,”

“Great,” Her eyes flicker out of the window.

“Y/N,” Dean says softer. It prompts her to look back at him, “It’s also  _ your  _ wedding and even though we have to have all those idiots attending, I want you to at least be comfortable. Do what you have to, okay?”

“Yeah,” She nods, not exactly knowing how comfortable she’ll ever be with a wedding that she has no hand in planning, and it’s with a man who pays her to do it.

Dean’s hand inches to the back of her head, curls his fingers around her neck, and pulls her close. He draws her in, kisses her forehead, “Good, because I need you to be in this, alright?”

She nods her head. She knows. She is. But she still feels the pressure.

They walk over to Sam who reads aloud the press release he just wrote up. It’s going to be all over the news as soon as he hits the send button, so she has to act fast. Also, she’s sure that Jimmy will haunt her ass once he knows, but that’s something she’s going to deal with later. Her priorities are Liv and Bobby for the time being. And someone else.

“Right,” She pats down on her thighs, “I have to go see what’s going on upstairs,”

“Yeah,” Dean stands up with her, walking her to the door. He holds her back by her wrist before she’s about to slip out, making her turn around before he places a hand on her cheek, brushes his knuckles over it gently, “You’re going to be okay?” 

“Yeah,” 

She’s not right now, but she definitely will be okay. It’s just really the shock that’s still sitting in her bones and it will probably take some time for it to wear down. Things will calm down once she can let it sink in. Or maybe, they’ll get worse, the jury’s still out on that one. 

He presses a kiss to her cheek before she leaves, lingers there and she leans into him, melting against him, as it has become a reflex now. His scruff tickles just the right way.

“I’ll finish earlier, okay? We can go out, get our minds off of this for a little while,”

“Yeah, sounds good,” She nods, hoping he doesn’t see that she doubts it. Doubts that she’ll ever be able to think about anything else. 

  
  
  


*

  
  
  
  


Y/N leaves Dean’s office, but instead of taking the elevator up, she takes the one that’s going down. 

Arriving on her old floor, she’s greeted by familiar faces who look at her like they’re seeing a ghost. Already people are talking behind her back, but she doesn’t hesitate and stalls around. Instead, she walks right into the open space office, finds her desk and is surprised that it’s still empty. She guesses since Dean fired her supervisor, his position will be filled first and since he also fired the head of HR, the recruitment process will most likely take a little longer.

“Hi Donna,” She greets her friend and the blonde woman looks up at her. There’s a slight frown on her face at first, but it gives way to a big bright grin pretty quickly. The woman’s grin was always contagious and Y/N grins with her.

Donna immediately jumps up from her chair and attacks Y/N with a big hug. It almost squeezes the air out of her lungs, almost making her topple over on her heels, but she manages to steady herself. God, she had missed those hugs. The real ones from real people. Not the weak handshakes she gets from rich people.

“Oh my god, I’ve missed you!” Her friend shouts out, has a hard time keeping her giddy voice down.

After the initial greeting, Y/N sits down on her old office chair that she rolled over to where Donna’s sitting and informs her friend about her wedding on Sunday. The woman’s jaw is hanging down during the course of the information Y/N just slapped her with.

“I wanted to ask if you’re going to be my bridesmaid, or was it a maid of honor? I don’t really know, but you’re the only one so you can be whatever you want,” She narrows her eyes, pulls her shoulders up in anticipation because she doesn’t know how Donna will react. Y/N has also not been really frank with her friend, out of fear that people could overhear them. So, all Donna knows is that they'll get hitched this coming Sunday to Dean fucking Winchester.

To her surprise, Donna doesn’t ask questions. She can sense that her friend knows that there’s more to the story but Donna’s not an idiot. Donna will never push her when Y/N doesn’t want to be pushed. And she’ll tell her, she will. Just not here and not now.

“Of course! Oh my god, this will be super fun!” The woman giggles.

Y/N should have known that Donna will be more than delighted. Especially when there’ll be some celebrities attending, since her friend is a slut for tabloid celebs and is dying to meet one of them in real life for ages. The closest she got was seeing Dean from across the floor when he was down on their floor one morning for a meeting. Y/N remembered her friend not being able to work for at least five minutes because her hands were shaking so badly.

“Are you happy?” Donna asks. The question catches her a little off guard.

Is she? Happy?

She doesn’t really know. She is, in a way, she supposes. It has been better than she thought it would be, apart from the fact that Jimmy is a pain in the ass, but Dean’s been sweet to her and it’s so much better than what she was hoping for at the beginning. The only downfall is that she fell for Dean knowing that he will never be able to reciprocate her feelings. But does he really have to? He’s right, it’s a win-win for both of them. As long as he treats her with respect and keeps the overall caring nature that he has, she guesses that’ll be enough. She knows that she’s kidding herself too, but she’s had it worse. Maybe this is all she’s going to get and she should maybe be thankful for getting a chance at something just like this at all.

So she nods her head, “Yeah, I am,”

“Good,” Donna winks at her and she stands up, places a hand on her friend’s shoulder, giving her a squeeze. Donna lays her hand on top of hers, squeezes her back, “I’m happy for you.”

Y/N smiles warmly at her friend, “So, I was thinking, if you have nothing planned, why don’t you come up? We can spend some time together with Liv?”

Donna’s face lights up immediately and a little guilt washes over Y/N because she was preoccupied with her life and not once asked how Donna was. 

“I’d love to.”

  
  
  


*

  
  
  


As soon as Donna stepped into the penthouse, her eyes widened and her mouth stood agape. 

“Holy shit, Y/N!” Her friend squealed.

She could only smirk at the blonde's reaction. 

They settled outside as soon as Y/N showed her friend the whole house, and all the while Donna was giggling and she couldn’t stop the jabs against how rich people live. Y/N’s doesn’t think it’s rude. She felt the same when she started to live here and she needed some time to get used to it.

“So, you want to tell me that you get paid for this?” Donna asked after Y/N poured her heart out. It felt good. Great even. At least she now has someone else beside Bobby to confide in. She thinks it’s totally what she needs. There are just things that she can only tell Donna and there probably will continue to be things that she only can tell her friend. Maybe Sam would want her friend to sign an NDA but she trusts her.

“Yeah,” 

“And he’ll keep paying you for being married to him?”

“Uh, yeah. Although I talked to Sam and we agreed on a fixed sum.”

Y/N talked to Sam this morning when he came to get her for the board meeting, telling him that she feels like she’s taking advantage of Dean if he wants to keep on paying her $2,000/day as she’ll be living for free and all.

Donna snorts, arms coming up to secure her ponytail tighter behind her head, “I bet it’s just a fraction of what you would get, isn’t it?”

“I feel bad for taking money at all, Donna,”

“Ah, that’s so  _ you _ , you know?”

“What?”

“Yeah, Y/N,” Her friend grins, “That’s so you. You’re too nice. I guess Dean can be really glad he picked you and not some money greedy bitch.”

_ Picked you. _

The talk she overheard with Sam is pushed to the forefront of her mind. She’s the first one Dean picked by himself. She desperately wants to think that it means something. But it probably doesn’t. She was never lucky with men and somehow with Dean, she lucked out. Not that he will ever love her, but he does care. So at least, there’s that.

While she’s lost in thoughts, she must have zoned out, because Donna nudged her elbow into Y/N’s side, “Hey, you still with me?”

“Huh,” She looks at her friend, “Yeah, sorry,”

Donna sends her a knowing look, the one where she tilts her head to the side a little, and her lips are turned up into a crooked grin, “C’mon, spill!”

“Spill?”

“I know you, Y/N. There’s something you don’t tell me,”

She tries to look anywhere but at her friend, her fingers play along her jeans, nails scratching at the denim’s surface as she tries to form words in her head and think about how to spill out what’s in her heart. She shakes her head, can’t believe it herself how she bottled up the feeling for so long without letting it out. Sighing audibly, she looks over to Donna and something clicks in her friend because she starts to talk first.

“You feel something for him, don’t you?” Donna says it with a warm smile and places her hand on Y/N’s restless one on her thigh. 

“I shouldn’t,” She replies.

“Why not?”

“Because he’ll never feel what I feel.”

Donna frowns.

“Yeah,” Y/N sighs, “He said he’ll never be able to love me.”

“Ah, that’s bullshit!” Her friend exclaimed, throwing both her hands in the air, landing on the woman’s thighs with a thud. 

“It’s true.”

“He said that?”

“Loud and clear,” Y/N nods, “He said he’s never been in love and he will never be in love. He said it when I signed the contract.”

Donna stands up from the couch and braces her hands on her hips, “It doesn’t mean it can’t happen, Y/N.”

“I don’t want to get my hopes up,” She shakes her head, “And besides, maybe it’s good like this. I know what I’m getting myself into, I know that I can’t expect him to love me back. As long as he cares, maybe that’s enough?”

It shouldn’t have come out as a question. Her voice did it on its own. It sounds bad. Like she wants to convince herself that it’s enough when she knows deep down that it isn’t.

“Is he being good to you?”

“He is,” It comes out much too quick but it’s the truth, “He’s so good with Liv and the little girl loves him to bits.”

Donna smiles, “That’s good. Liv is never wrong with people.” 

“True,”

“So, why not embrace what you have, Y/N? I think you deserve something good in your life and Dean is good from what I gather. Take a little happiness for yourself, okay? And who knows? Maybe you can change his mind?” 

She snorts out a laugh, “Yeah, like if that’s going to happen.”

Little does her friend know that she already took plenty. At least she takes what Dean’s willing to give her. She wonders if he will really never give her all of him.

“But at least you can say that you bedded the hottest entrepreneur of 2020!”

“Donna!” 

_ Technically _ , that’s not entirely true, but she’s not going to spill that one.

The woman giggles, “What? I always wondered how big he is. Is he big?”

“Oh my god,” Y/N groans and she remembers his hardness in his underwear when she ground on it this morning, “Well, he is.”

Donna’s mouth stands open, “Oh my fucking god, you two already—”

“—No!” She interrupts quickly, “No, we haven’t. But we’ve done other things.”

Her friend lets out a squeal, “Look at you, taking what you need, huh?”   


“Donna,”

The woman shrugs, “Hey, I’m not judging, I just think it’s great that one of us has any action at all. What’s he like?” 

“Donna!”

“What?” 

Y/N rolls her eyes and shakes her head, thinking Donna will probably let it go, but when she looks at her friend, Donna’s still grinning at her and she even wriggles with her eyebrows.

She groans, “Right, he’s a very good kisser.”

“I can imagine,” Donna swoons.

“Like  _ really  _ talented tongue,” Y/N goes on and Donna’s eyes widen, “And skilled fingers,” 

Her friend's eyes almost fall out of her eye sockets and the woman opens her mouth to speak, but another sound distracts the both of them. 

“Mommy, the tea party is ready!”

“Coming!” She calls out to her daughter, grinning at Donna who’s still trying to process the information Y/N has given her.

  
  
  
  
  


_______________________________________________________

  
  
  
  
  


It was almost impossible to work after Sam had sent out the press release. The tabloids picked up on it fast as lightning, calling Sam and his company to get an exclusive interview, which they obviously don’t give them. There’s really nothing to say. They still haven’t found out who Y/N really is, and Dean thinks he wants to keep it this way. He owes her and Liv that much.

Dean’s never been a fan of the press. He usually plays along as long as it helps boost his business but other than that, he thinks that they are vultures that feast on people’s souls. It’s too easy to get eaten up when they are fawning all over you, too easy to get spat out when you’re not interesting to them anymore. 

The only good thing in all of this, Dean guesses, is that the venues keep calling him as well. They sent him emails, asking where the wedding will be held and some were willing to organize everything for him if he chooses their establishment. That’s one of the perks of being tabloid famous, he guesses, and right now it comes in super handy.

He opts for the Ritz, not only because he gets a great discount and their PR is Charlie, a good friend of his and Sam, but also because it’s two blocks from his company/penthouse. He also doesn’t take their offer for rooms, thinks that Y/N will probably want to get back after the festivities and maybe Liv would be happier to be sleeping in her own bed with her stuffed animals. But also maybe he’ll whisk her away after it’s done. He’s sure everyone will be having an eye on them to see where he takes her for their honeymoon. He maybe should get on that, even if he knows that Y/N probably doesn’t even want to get away.

At least now the weight of sorting out the venue is off his shoulders. He gets his secretary Rowena in, tells her to organize the rest and always makes sure to ask Y/N if she’s okay with Rowena’s suggestions. Dean really doesn’t want more people involved, thinks that maybe Y/N would want to help organize her own wedding. Because that’s the dream for most women, no? At least for those who have always dreamt of a big fancy wedding. He has no idea if she had such ambitions when she was younger. All he knows is that he doesn’t want to keep her out of the loop, he owes her that much after she blindly agreed to become his wife. 

_ Wife. _

It just hits him now. He’s going to get fucking married to a woman he barely knows. She’ll be his fucking wife.

Strangely, though, the term doesn’t scare him or throw him off at all. It could have been much worse, not that this is bad, but he just thought that he would have ended up marrying Carmen for example. A woman who can’t look past her own nose. Their marriage would have served one purpose. He would get the shares, she would get prestige and maybe he’ll get humiliated because Carmen is less than discrete with her hookups.

With Y/N, it’s a whole other story, and he thinks the choice he made has been the best in his life yet. She’s different. She genuinely cares about him. And he reciprocates it in the only way he knows how. He’s going to make sure that Liv’s future will be bright and they are both cared for. 

Hell, he even toyed with the idea of adopting Liv, would do it in a heartbeat if Y/N would be okay with it. They could be a little family and Dean’s not displeased by the prospect of having them around all the time. On the contrary, he honestly enjoys them so much that he can’t imagine not having them around anymore. 

So much for not getting attached, huh? Y/N said she didn’t want to let her child get attached to him, but there was nobody warning him how much he can get attached to a child and the child’s mother.

Not to mention the sex they aren’t having. It’s getting harder and harder for him to keep his dick away from her pussy. Especially now that he knows how she feels around his fingers, knows how she tastes on the tip of his tongue. His self-control is hanging by a fucking thread, the sounds of pleasure he coaxes out of her works like a knife.

Y/N’s going to be Mrs. Winchester in six fucking days. 

_ Mrs. Winchester. _

Somehow, it doesn’t sound bad at all.

Sam leaves after he has sent out the press release, with a promise to have the amendments to her contract ready by tomorrow, and Dean still has four meetings to attend, even though he has the urge to go up to her, to see if she’s really okay. He looks over his schedule, sees if he can cancel, but it’s almost impossible as they require his attendance. Maybe he’ll cancel other meetings during the week, Dean thinks, as he clicks on his calendar, rearranging meetings to kill the time until his next one. 

  
  
  
  


*

  
  
  


Of course every time Dean is determined to leave earlier, there’s always something coming up unexpected and by the time he can go up to his penthouse, it’s already 7 PM. 

He walks around his apartment, searches for a sign of Y/N. The door to Liv’s room is wide open, music blaring out of it. He smirks as he walks closer, peeks around the corner. 

Dean chuckles and leans his body fully against the door frame as he watches the girls dance. Another woman is with them. His brain needs a minute to dig and search for the name because he’s sure he’s seen her before. When his brain registers, he smiles.

“My two favorite girls,” Dean states, as he leans against the doorframe, “And Donna.”

It’s all true. They really are his favorite. But also he didn’t think that Y/N would catch on, wouldn’t think that she’d hear it above the music, but she does and stops spinning. Her cheeks are flush and Dean’s not really sure if it’s because of what he said or of them dancing around. But she looks so fucking cute he almost can’t stand it.

Her mouth opens, he’s not really sure if she wants to say something but then there’s a shriek from Liv as the girl charges towards him, jumps right up into his arms and Dean catches her on instinct. He steps into the door, spinning the little girl around as she giggles. 

He keeps Liv in his arms as Y/N and Donna walk towards them. 

“I’ll just be outside,” Donna says and squeezes past him, “Nice meeting you, Boss.” The woman grins. 

“Call me Dean,” He sends her a courtesy nod.

“I hope it’s okay that Donna stayed this long?” Y/N asks Dean. He looks back to see a frown on her face.

“That’s fine,” Dean answers, “It’s your home too, you can invite anyone you like,”

She nods.

“Have you?” He asks when there were just the three of them, doesn’t want to push out the whole question in fear she hasn’t and Liv would have heard something from him that she wasn’t supposed to. 

“Yeah,” She smirks, “Bobby’s mad at you.”

“He is?”

Ugh. He doesn’t know why he’s so fucking nervous now. Bobby’s mad at him. Dean feels like his insides are squeezing him. He might feel nauseous too. Maybe, he should have asked Bobby first? Which is actually ridiculous because it’s not fucking real and now he doesn’t know why he’s sweating.

Y/N starts to chuckle, “Relax, big guy, I’m kidding. Although he did say that he would have married you too if you needed another wife,”

“Jesus, Y/N,” Dean grumbles but keeps himself in check because Liv’s still on his arm. He lowers himself and lets her out of his grip, keeps himself on his knees to speak to the girl, “Are you okay with me marrying your mom, Liv?” 

The girl wraps her arms around Dean’s neck and attacks him with a hug, sending him landing on his ass as he laughs. Liv’s laughing too.

“Yeah,” The girl says brightly. 

It makes Dean’s heart swell as relief washes over him. He never knew that a little girl’s opinion could weigh so much on his heart. Somehow, Liv being okay about it, is all that counts. 

Before Dean knows it, Liv opens a round of tickle fights. 

  
  
  


*

  
  
  


Dean’s sitting in a club. Sam called earlier, said it would be great if they could go out and let the press take pictures of them together after the announcement today. 

It’s definitely not Dean’s thing to go clubbing during the week, but it’s the only way really, Sam isn’t wrong. 

The only club that is always frequented by photographers is  _ Euphoria _ . Dean’s friend Cas owns it and they get a secluded place in the VIP section which overlooks the dance floor where Y/N is currently dancing with Donna. She asked to come along and Dean’s actually glad to see Y/N having fun with her friend. He’s been hogging her since she came to live with him, he knows that, so it’s actually very refreshing to see her having fun besides going to lame outings with him, which he doesn’t really want to be a part of either. 

So, it’s actually pretty good to see her letting loose, to see a genuine smile on her face rather than the forced smile they give to the world when he drags her to a party he knows she doesn’t have fun at. He does have fun there, but only since he has her around. They can be silly and make fun of the snobs. He didn’t even know he needed her until she came into his life.

So, right now, Y/N is dancing with her friend and Dean sits on the couch on the VIP level, watching them having fun from up here while simultaneously trying to do some work on his phone. He didn’t get to finish a lot today with the announcement and all the distracting phone calls from press and venues. 

It’s not like he can concentrate here either, though. At least not when she’s swaying her hips down there in her short dress and high heels. The dress screams _ ‘Dean Winchester’s fiancée’ _ , no doubt about it. He dated or at least showed up with a lot of girls dressing like that, but honestly, and he doesn’t know what comes over him, but he loves her dressed-down look more. The way she stood in the kitchen with cookie batter smeared on her cheek and an apron draped over her oversized shirt, that’s the look that does things to him, even though he knows that it shouldn’t. 

The dress is strapless too, and Dean could see that she had tried to conceal the mark on the swell of her breast that he left there the previous night. It works just a little, though, the bruise that his mouth inflicted is still visible at least when you know that it’s there, and it irritates the fuck out of him because he’s kinda super proud of that one, even though maybe he shouldn’t be.

When he glances down to the dance floor the next time he tears his eyes away from his phone, she waves at him, signaling for him to come down. Dean lets out a sigh and rolls his eyes dramatically. But he can’t seem to say no when she pouts so damn cute. 

Yep, still can not stand it when she’s cute.

He stands up from the couch, empties his glass, and walks down the steps. His eyes are on her, sees her pout making way for a bright smile.

A smile of a winner. He recognizes one when he sees one.

“Hey,” He says when he comes to stand next to her and she throws her arms around his neck, kisses his cheek softly. His arms go around her waist instinctively. She’s apparently a little tipsy, judging by the way she clings to him. 

“We should probably not separate for so long,” Y/N whispers into his ear and yeah, she’s not wrong.

“You wanna dance?” Dean asks her, one of his eyebrows raised.

Donna is turning away from them, dancing with a guy who he thought was interested in Y/N at first, or maybe he wanted both of them, which honestly, Dean respects him for the boldness, but the guy immediately turned all his attention back to Donna, probably thrown off when Dean joined them. Good. Guy probably wants to keep all his teeth in place for the time being.

“You know I can’t dance,” She whines, but there’s a smirk on her face, like she’s not really embarrassed that she can’t dance, “I’m just swaying a little while Donna does all the work!”

Yeah, he noticed. It’s super cute because Donna clearly has rhythm whereas Y/N lacks it, but she’s trying and that’s actually adorable.

Dean grins smugly, “Come on,” He says as he takes her hand to lay it on his shoulder. They stand there with his hand on the small of her back, his other holding hers. He pulls her closer, presses her body to his, leaving no space in between. 

Y/N frowns up at him, “I don’t think the music’s right to dance like that,” 

The smug grin is still on his face when he winks at her, “Wait for it, sweetheart,”

Her eyebrows knit together adorably. Dean can’t stop grinning when he lifts the hand from the small of her back and signals that he’s ready.

Suddenly, the loud bass gives way to easy tunes and Eric Clapton's ' _ Wonderful Tonight’ _ starts to play. 

He can see that she’s trying to hold on to her irritation, but it runs away from her. 

Snorting out a soft chuckle, she shakes her head, “You didn’t,”

“Did too,”

Her eyes shine with that glint he came to cherish when he starts to sway her to the tune. Usually, Dean’s super aware of his surroundings. He hates to make a fool out of himself, hates to know that his image gets stained because he did something stupid, that people will talk when he wasn’t being careful, but now is different. With her, it seems like he doesn’t care about it as much anymore. At least not how he should. 

He pulls her even closer, feeling the softness of her body against him, somehow wishing there wasn’t a stitch of clothing between them. He’s a little ashamed that he’s half-hard from the closeness alone, thinks she must be feeling it too. She has her forehead rested on his throat while he nuzzles his face against her temple. 

In this moment, everything and everybody else is forgotten.

“You think you’re so slick, Mr. Winchester,” Y/N whispers. He can feel her hot breath against his skin.

Dean shrugs, “Sweetheart, I don’t  _ think  _ it. I  _ am  _ slick,”

She chuckles and they sway until the song stops. When it ends, everyone’s clapping, but he still doesn’t take notice because all he sees is her. Dean stands back to look down at her. His heart drums in his chest, wonders if she’ll kiss him, and feels his heart stopping when she finally does. 


	18. Chapter 18

“You don’t look like you’re having fun.” Y/N’s voice makes Dean look up from his phone.

After the slow dance with her, he let the girls have fun together while he retreated back up here. But he didn’t leave without sending a glare at the dude who was dancing up to Y/N before. He thinks the guy got the memo though as he stays well within the line, keeping himself firmly pressed to Donna and Donna only.

Taking a look at the little bar above the email app Dean has open, he can see that an hour has passed since then. 

A glance down to the dance floor confirms to him that Donna has her lips locked with the dude, and that’s probably the reason why Y/N came up here. 

Letting herself fall onto the couch next to him, she takes off her shoes and he chuckles, slipping his phone back into his pant pocket. The email he was writing up is still unfinished but she’s a welcome distraction. 

She drapes her legs over his thigh, wriggles on the couch to be closer to him and Dean reaches out, pulls her into his side, her head rests on his shoulder. It’s crazy how easy it is. Either he’s really getting good at this pretend thing or it’s not an act at all. He still doesn’t know. Kind of afraid to know, to be honest.

His one hand strokes her bare thigh. By now, touching her feels normal. He wouldn’t want to change a thing. “You done dancing?”

“Yeah, Donna’s getting lucky tonight and it seems like she doesn’t need me anymore,” There’s a playful pout on her lips. It’s not a real one. Still, it does things to Dean, things he can’t really put a finger on.

He chuckles and quickly lifts her up so she lands sideways in his lap with a squeal, “Her loss is my gain, then,”

It’s easy saying things like this, Dean realizes. He’s never been very good at it. Flirting he can do, but this isn’t flirting. When he flirts, he knows what he wants, and often, he gets his way without even having to try too hard. This, though, this is something else. It’s not flirting when it’s fake, is it?

His hand is on her thigh, stroking her there, still. She’s so soft underneath his palm. It gets a reaction out of him but he’s controlling himself. 

Dean lays his face to her arm and she jerks away briefly. It’s because of his beard, he thinks. It must be pricking her skin. But she wanted it like that, now she has to lie in the bed she made. 

Placing a soft kiss to her skin and pressing his face deeper against it, he holds her when she squirms again and Dean chuckles before he speaks. The music is loud, but up here it’s bearable. They can hold a normal conversation without having to scream their ears off. “You okay?”

She turns her gaze from the dance floor back to him and hooks an arm around his neck and shoulder. Leaning in, she presses her lips to his temple. Her hand behind his neck strokes at the short hair on the base of it. If she only knew how fucking crazy she drives him with the gesture. It’s actually pretty intimate and even though he never lets himself get too close to intimacy, he can’t lie that he likes it. He never realized that he actually craved for it until now. And again, the thought should frighten him, but it’s strange that it doesn’t.

“Yeah, I am. Are you? I mean, are you still okay marrying me?”

Dean’s a little taken aback by her question. Doesn’t understand why she thinks he wouldn’t be when it’s him who basically coerced her into it. 

“More than okay,” He assures her. He’s happy to see a smirk on her face when he says it.

“Really? Even though we’ll probably stay married for only a couple months after?”

“Yeah,” He says, keeping his thoughts about not wanting a divorce out of his mind for the time being.

“You just really have to be careful when you screw around, otherwise your face will be all over the tabloids for cheating on your wife.”

Ah. He can literally hear the coin drop in his head and he snorts out a laugh, can’t possibly  _ not  _ because it’s too cute how she tiptoes around it. 

Leaning back into the couch, Dean brings her along with him. The weight of her on top of him is comforting. Her forehead rests on his cheek, but he pulls away to look at her. Their eyes meet. He can see that they aren’t as clear as they usually are. There’s something troubling her. Slowly but surely, Dean’s able to read her.

He brushes his fingertips against her cheek, his thumb paints along her lips. “I’m not a cheater, Y/N. Never have been, never will be. If I’m in a relationship, I take it pretty seriously.”

“‘S that way you never  _ are  _ in a real relationship?” She mumbles and he feels his thumb moving on her lips.

“Touché.” Dean snorts out a chuckle. She has him by the balls, not letting him go easily.

“Just saying,” Her voice is a little lower, “Be careful,”

“Y/N, I’m being serious,” He drops his voice a little, maybe to make a point. His hand strokes her thigh, up and down. Her skin gets bumpy underneath his touch, “Once we’re married, it’s you and me. You’re mine and I’m yours.”

She leans in closer, brushes her nose against his playfully. He can’t see her eyes because of their closeness, but for a flicker of a moment when she closed in, he could make out the glint that’s usually there when she looks at him. He really doesn’t want to fucking hurt her. Thinks that he might not have to hurt her after all when they are both clear and know how things are before they go into this. Maybe, Dean thinks, when they both know what they want, it’s not bad right? Sex without feelings is the only thing he knows anyway. 

Then he feels it, the pinprick in his heart when her lips brush against his. It’s soft, so fucking gentle. He feels like he doesn’t deserve it.

“Does that mean that you’ll fuck me?” Her voice is playful, there’s a laugh accompanying those words. It’s more inciting than it’s dirty.

He has to laugh at that. She’s totally needy. Not that he minds. It’s just too cute and he still can’t fucking stand it. 

This time it’s him who kisses her, tongue teasing along her bottom lip. His hand on her thigh inches up, disappears beneath her dress. He licks into her mouth that she parts for him. It’s easy, he thinks. But also it’s no wonder, sex has always been easy for him. It’s the feelings that he has a hard time understanding and sorting.

The tip of his finger grazes her underwear. It’s lace. He wonders what color it is, if it’s one of the many he bought her. 

Y/N whimpers into his mouth when she feels his digit rubbing along the fabric. And she even parts her legs for him. What a fucking good girl.

They’re in public. He’s sure that some will get pictures of them up here, and yet, still, it feels like they are the only ones in this club. Meaning basically, that he doesn’t give a rat's ass if he’s caught with his hand up his fiancée’s dress or not. Which again, should fucking frighten him because he never let himself have public exploits before. Strangely, again, it’s more exciting than frightening.

Dean smiles into the kiss, “Would you like that?” Well, to be fair, he knows. She’s shown him enough how much she wants him, but he just really, really likes to hear it. 

She’s still hesitant, doesn’t answer him right away and Dean teases her some more, just because he can. His one finger rubs down her center, still above the fabric but it might as well not be there because she has fucking  _ soaked _ it through.

“Fuck,” He curses, bites the inside of his cheek because seriously,  _ fuck _ . He hasn’t done a thing and she’s dripping. He swallows down the noise he’s about to make, clears his head with a shake before speaks again, “Tell me baby, would you like me to fuck you?”

Cradling his face in both her hands, she breathes out a “Yes,” before she kisses him. It’s rough and hard this time, something he’s not really used to with her. At least not when she’s initiating it. He can’t really say that he minds. On the contrary, his dick stirs and gets harder at her sauciness. She sucks on his tongue sharply and he holds his breath as much as he’s holding himself together because that alone makes him want to fuck her right here in public.

Something he knows he can’t. Right now, his head is still being more reasonable than his dick, and he knows that he should keep it that way. Dean can’t stop slipping his finger into the crotch of her panties, though, wants to feel the slick of her on his fingers. 

Yep. She’s dripping wet. He doesn’t slip the finger in her pussy, though. Can’t risk being exposed for indecent behavior in a club right before their wedding. It wouldn’t look really good in the papers, he supposes. Not that  _ he  _ cares that much, but he’s sure that  _ she  _ does care because he can’t imagine her wanting Olivia to find out about this one day. Once things get on the internet, they, unfortunately, stay there and no money in the world can erase that.

Dean pulls his finger out, comes up with it and holds his wet fingers between their faces. The heady scent of her is strong between them. Y/N bats her lashes. It’s a new look on her. A look that’s going to kill him one day, he just knows. 

Her fingers curl around his hand as she takes his wrist and places the fingers to her lips. She sticks her tongue out, licks at his finger, eliciting a groan from him, even though he tries not to. The last shred of self-control that he’s clinging on to is surely slipping away, and Dean tries to grab at it, he really does, only, it’s not working when she sucks his fingers in and twirls her tongue around it. It’s absolutely fucking filthy, but he fucking loves it. 

“How do you taste?” He asks when she pops his fingers out of her mouth. Dean's voice is gravelly, just a tad deeper. He tries not to moan at the images of her sucking his cock instead of his fingers. It was so hard to control himself right now and is glad that he doesn’t really have to. Not after he held himself back the previous nights. 

“Good,” She answers him with a smile and that’s doing him in. He surges forward, licks hungrily into her mouth because he wants to get the taste of it as he fucking knows how she tastes and he doesn’t think it’s fair that she’s not fucking sharing.

When Dean’s able to think straight again, he breaks the kiss and pulls his face back. His thumb traces patterns on her cheek. 

“We have to be on the same page about it, Y/N. I will never be able to give you more than what I already give you now.” He tries to reason, tries to make her understand. It’s not that he doesn’t want to, it’s more that he can’t. He fucking can’t let himself go there.

She nods her head with determination in her eyes, “I know,”

“Good,” He nods back and smirks, “If you want me, Y/N, you can have me. All of me,”

Her forehead is on his as she tucks her lips between her teeth playfully. Her fingers start to trace lines and circles on his chest on the fabric of his shirt. “Do you want me?”

Dean can’t remember ever  _ not  _ showing her that he didn’t want her. So he chuckles and takes her hand, places it right to his crotch where his cock is straining against the zipper of his dress pants. He’s so fucking hard from simply kissing her, it’s unreal. She gasps, making Dean chuckle some more.

“That’s how much I want you.” He breathes out raspily.

Y/N’s eyes widened for a brief moment after her initial shock to find him so hard he could pound nails. Her gaze softens before she settles to an easy grin, “I think we should go home.”

Dean snorts out a breath, and groans out playfully, “Thought you’d never wanna leave.”

  
  
  
  


*

  
  
  
  


He presses her against the elevator wall, sets her on the metal railing as he kisses her hungrily. It’s all tongue and teeth, turning him on so fucking much. Her panties are discarded, stowed away in the pocket of his suit jacket. Y/N’s taken them off on the way back with a laugh. She’s tipsy. Dean almost thinks twice about fucking her but she’s seen her drunk before and she’s not on that level. He really doesn’t want to take advantage, but he guesses that she’s still in her right mind. Besides, he made her drink a bottle of water on the way back, saying he wouldn’t start the car before she emptied it. She did so with a pout, making him want to take her right there.

His dick was painfully hard on the way to the penthouse, driving torturous to say the least. Even more so when he knows that she’s pantiless, wet and dripping next to him.

Her legs are wrapped around his waist right now, his fingers rubbing her slick cunt as he kisses her as if his life depends on it. Her nails dig into his shoulder and the back of his head, when he slips two fingers into her pussy. 

Dean curves them just right, rubs at her wall on the inside while he thumbs at her clit. She moans into the kiss, signaling for him that he’s doing things right and Dean likes that. Likes knowing that he does things right for her.

“‘S that okay?” He whispers.

“God, yes,” 

“Wanna see if I can make you come before we reach the penthouse, baby,”

“Fuck,”

He drops his head to suck along her throat, “Can you take another finger, yeah?”

She nods above him, her chin hitting his head. 

“Good,” Dean sucks sharply at her pulse point, “Gotta prep you to take my cock, baby,”

“Oh god,”

He chuckles. He’s telling her the truth, though. He would not want to hurt her. Dean eases in another finger and it’s a fucking tight fit. He can barely breathe, thinks if she’s hugging his dick like she hugs his finger, it might fall off. 

She’s getting so fucking soaked. The wet sound of his fingers fucking in and out of her is loud in the confined space. The wetness already runs down his wrist, soaking the arms of his shirt and suit jacket. It’s the fucking best.

Dean’s other hand goes up her front, pulling down her dress, revealing those fucking magnificent tits he’s dreamt of more than once. He kneads each of them roughly, feels her hard nipples underneath his palms.

“How do you feel, Y/N?”

“Fuck,” She curses as Dean curves his fingers just right, “So full,”

He chuckles as he feels her clenching around his fingers. She’s so fucking close and they’re almost up to their floor. Making her come before they arrive is going to be a challenge, but Dean’s never one to back down, “Just wait til I fuck you,” 

There’s a tight clench again and he doesn’t know if she’s excited about the prospect of getting fucked or if it’s because she’s close. Maybe it’s both. He lets himself believe that it’s both.

To test it, he fucks her faster, digs his finger into her wall and rubs over the button that makes her fucking crazy once more. He abandons her tits to rub over her clit with his other hand, pressing down the heel of his palm too and she’s squirming.

“Dean, fuck—, I—”

“I got you, baby” He growls and sinks his teeth into the place where her shoulder meets her throat. It looked so damn inviting.

Jesus, there’s the clench. The fucking tight clench of her pussy. She’s coming hard, he can just feel it. Risks a glance up to see her eyes crossing. It’s absolutely cute, almost tips him over too. 

There’s a squeal of delight when she comes, like the one he’s heard before. The one he can never get enough of, and Dean just can’t look away because she looks absolutely amazing when she comes apart, but he’s getting side tracked by the gush that soaks his hands and it’s even on his goddamn pants because she fucking squirted.

The whole wall where she’s propped up against and the floor of the elevator is a mess.

“Jesus, Y/N,” He croaks out breathlessly.

The elevator dings to signal their arrival. The door opens but they don’t get out. Instead, she looks down to herself and is completely horrified by the things she’s seeing.

Dean slowly slips his fingers out of her cunt, the water comes running out of her and he shakes his hand to release the excess wetness before he dries it on his dress pants.

Upon seeing the mess she made, she’s quick to bury her face into the crook of his neck. 

“I’m sorry,” She whispers against his skin.

“Hey,” Dean smirks, thinks she’s being too adorable, “Look at me,”

She does, albeit reluctantly.

Dean steals a kiss while she pulls her dress back up to cover her breasts. He thinks it’s a shame they have to be covered at all.

Pressing a kiss right on the pout that appeared on her face, he smiles when he looks at her, “Don’t be embarrassed, okay? It’s the hottest thing I’ve ever seen.”

He isn’t even lying. He’s never made a girl squirt before, not that he hasn't tried.

“Yeah?” She asks, the voice of uncertainty. 

“Yeah,” He tries to smile brighter.

“I’ve got to clean this up,” 

Dean frowns, “You really want to clean out an elevator when we’re about to fuck?” He’s laughing now, can’t believe what he’s hearing but the thing is, that he’s absolutely certain that she’d do it. He wouldn’t put it past her, and he’d rather not waste more time, feels like he should be inside of her yesterday. He tucks a strand of hair behind her ear, places a kiss on her cheek to calm her down, “I’ll text the cleaner to start with this elevator, okay? He starts at 5 AM. No one will even know.”

“‘K,” She mumbles Dean helps her down the railing, pulling her dress down a little to cover her naked ass and the pussy he’d like to have a taste of. 

Pushing the button, the elevator opens again and he guides her out. He keys in and opens the door for her, however, when she walks in, he catches her wrist to spin her around, presses himself up to her, kisses her for all he’s worth. 

Dean scoops her up after, throws her over his shoulder and she giggles at that. So much that he has to spank her hard to keep her mouth shut. They really don’t need to wake Bobby and Liv. Mainly because he wouldn’t have the patience to talk himself out of what’s obviously happening and he knows that the moment would be gone for both of them if Bobby or Liv would walk out into the hall.

  
  
  


_______________________________________________________

  
  
  


Y/N’s hanging over his shoulder, her legs dripping wet. Dean’s hand is firm below her ass, gripping at her thigh to keep the balance and keep her from squirming at the same time. It’s weird. He carries her like she weighs nothing and strangely, he makes her feel safe, like she just knows that there’s no way that he’ll let her fall.

He quickly walks along the hallway, walks through the living room, and goes straight for his room. 

As soon as he’s inside, he tosses her into the bed unceremoniously and she lands in a fit of giggles. The alcohol is wearing off but it’s still bubbling in her chest.

Dean’s quick to get into bed, kneeling down and pulls her against him by the back of her neck for a searing kiss. It’s more tongue and teeth than anything else. It’s pent up sexual frustration from all those previous nights. His hand tugs his jacket off, throws it carelessly away while he toes off his dress shoes. She hears them thudding on the hardwood floor. 

He trails his hand down her front, over the fabric of her dress, goes right up again until he reaches her throat, his fingers claw around it. He doesn’t apply any pressure, just holding her there and it’s more exciting than it is frightening. The weight and the warmth of his hand on her skin is enough to make her breath shorten. He groans as she doesn’t budge or tell him to back off, he bites her lips so hard it hurts afterward. She really doesn’t mind feeling the tightening of his grip or the bite to her lips. Didn’t even know that she’d like it until now.

“Tell me you want this,” Dean whispers hotly, almost pleadingly. His voice is all raspy as his nose nudges against hers, mouths hovering, breathing out warmly, “Tell me you want me to fuck you, Y/N,”

_ God _ , how can he think she doesn’t want it. She’s come this far and let him into her life, she’s not going to back down now. It’s frustrating, really. She’s only a woman and women do have needs. Pretending to be Dean’s fake fiancée when he turns her on so much is so damn frustrating, and she really needs for him to fuck it out of her. Maybe, she thinks, it’s going to be better after. Maybe, she doesn’t want him as bad as she wants him now. 

Y/N pulls her swollen lips between her teeth — swollen because of his kisses — and nods her head, “Yes,”

There’s a smirk on Dean’s face. She’s almost sad she can’t see the crinkles from up close. The only lightsource is coming from the dimly lit bedside lamps that came on automatically as soon as they stepped into his bedroom. 

“Yes, what?” The tone of his voice is playful, a little hopeful.

“I want this, Dean. God, I want yo—”

He claims her mouth before she can finish the sentence, bites down on that swollen lip of hers with a groan, tongue sliding in beside hers. The kiss is totally needy, totally what she craves right now.

Dean parts with a last tug of her lips to sit back on his knees between her legs. His hand goes to her legs, taking off her shoes one by one, pausing after he gets rid of one to place kisses on her ankles, nibbling at them with his teeth, making her laugh out loud as she tries to pull her leg away from his grip. He chuckles, not letting her go, bites into her ankle once more before he takes off her other shoe. It’s totally playful and she loves that.

As soon as he has both shoes off, he slots himself between her thighs, kisses up her leg, starting from the knees. His hand bunches up her dress, pushes it up so it’s around her waist, her pussy dripping and bare to him and she’s feeling super self-conscious but any attempt to close her legs is lost on Dean because he’s so broad between her thighs, leaving her no room to close up on him.

His beard scratches along the inner of her thighs and Dean lays himself down, pausing his kissing when he reaches her center to hover at her pussy. His eyes are on her when he breathes in.

_ Fuck.  _

It’s absolutely filthy seeing him do this and she might be a little embarrassed and totally panicking right now, but fuck, if she said it didn’t turn her on, she’d be lying. 

His eyes meet hers, as if he’s not really sure and needs her permission. His eyelids are hooded, his pupils blown. 

Y/N swallows before she nods. 

Dean growls at her confirmation before he leans forward, his tongue wide and warm as he sweeps a path from the place where she's dripping up her slit to her clit. He hums his approval upon tasting her on his tongue. It sounds so fucking sexy and she  _ knows  _ she could come from that alone if she would let herself.

He flicks his tongue around her clit, takes his time unlike the last time he went down on her, tests out what she likes by watching her reaction carefully. He changes between fast strokes and slow french kissing, his teeth grazing her hood, making it almost unbearable for her to keep her tingly feeling at bay.

“Dean,” She whines, as her hand goes to his head, threading them through his hair. 

Humming, he works his way down, fucks his tongue into her pussy and he adds his fingers too, trails the wet tip of a finger along her perineum. 

_ Shit. _

Nobody has touched her there before. She didn’t even know that she could like it but she does. Fuck, she does.

His other hand goes up her body, pulls her dress down that’s barely clinging on to her chest anyway, revealing her tits and he kneads at it, rolls her nipple between his fingers while he grinds against his bed to gain friction.  _ Jesus _ , he’s turned on. Eating her out turns him on and knowing that, rubs her all the right way. His beard is scratchy but it feels so good. Almost too good.

Dean doesn’t use his fingers on her apart from that one where he’s rubbing wetly over her rim. Still, she feels the pressure coiling inside her. Feels the curling of the toes on her feet that rest on his back. 

“Dean,” Y/N moans out shamelessly, hands finding his head, her fingers thread through his hair to hold him there, “Don’t stop, please don’t— fuck—,”

He doesn’t. Instead, her moans just urge him on more and he sucks her clit into his mouth, hums some for the right stimulation. Her thighs press together and she thinks she’s cramping down and locks his head in, but she doesn’t really know because her mind goes blank.

She pants heavily, her chest heaving as she regains consciousness, chuckles too while she comes back to her senses. The orgasm was less powerful than the first one he gave her tonight but it doesn’t mean that it’s less intense.

As always when she comes down, she starts to wear the biggest grin on her face. Looking down, her eyes meet Dean’s. He’s watching her as he laps lazily at her juice around her pussy, his face totally soaked. He closes his eyes, slurps in some more, moaning as he does.

He makes it seem that she’s so fucking tasty. 

“You taste so fucking incredible,” Dean growls as he noses at her clit, places a kiss on it too before he pushes himself up. “And I know I said I wanted to take my time but, fuck,” He sounds a little out of breath, “I wanna feel you around my cock. Would you like that, yeah?”

_ God, yes.  _ Well, he already took his sweet time, she thinks. How much time does he want to spend down there? 

The words won’t come out but she nods enthusiastically. 

With a grin that matches hers, he reaches behind her, unzips her dress that’s only hanging around her stomach and takes it off. 

She’s naked on his bed now and Dean leans in, his hand on the back of her head as he pulls her closer to kiss her. Her heady scent is strong on his face and tongue and she can’t do anything else than moan into the kiss. 

Dean doesn’t kiss her long though, pushes himself up and off the bed, his fingers hastily unbuttons his shirt, pulls from his pants, and adds it to the pile of clothes already thrown around on the floor.

Y/N covers herself a little. She feels so exposed. 

“No,” Dean protests, his voice is husky, absolutely sexy but firm, “Don’t. I wanna see you,”

Reluctantly, she opens up again, all shame and inhibitions gone. It’s not like he hasn’t seen her pussy or memorized her body with the tips of his fingers before. He knows what she looks like, and somehow, he makes her feel wanted, makes her feel like she’s really beautiful. And even though she seldom believes it herself, she does with him. It’s a gift, his charm, she thinks. He doesn’t even have to have feelings for someone, yet he’s still able to make them feel like they’re special.

“Good girl,” He shows her that lopsided grin and that’s doing her in.

Her pussy clenches at that. 

His fingers open up his belt buckle, unbuttons his pants and pulls down the zipper. He does it too slow, like he’s teasing her and it’s not fucking fair.

Dean continues to undress like he has all the time in the world, pulling his pants down first and then his socks. Last, he gets rid of his underwear, making his hard cock slap wetly against his stomach. Her eyes widen at the sight and she darts out her tongue to lick her lips. He’s so fucking hard from eating her out. It blows her mind. 

Spitting into his palm, Dean brings it down to stroke himself. Long, lazy strokes. Tantalizing slow. It’s totally filthy. It totally turns her on. She thinks he knows what effect he has on her because he grins smugly as he climbs back onto the bed, his dick hard and throbbing in his hand. He nudges at her thighs with his knees.

Dean leans down to kiss her, his tongue goes in deep, it still tastes of her. 

“What do you want, baby?” He asks with his forehead resting on hers.

What does she want? God, she wants him inside like yesterday. 

“Want you to fuck me,” She answers with a smirk on her face, pouts a little because he’s dragging it out on purpose and it’s not fair. “Please,”

“God, that pout,” Dean growls and leans down, nibbles at her bottom lip, making it hurt just a little before he sits back up, and that wasn’t fair either because it left her wanting more.

Y/N’s so fucking desperate, she doesn’t even recognize herself anymore.

His hand is on the base of his dick as he threads the tip through her wet folds, coating his whole shaft with her slick. 

“Dean,” She moans out at the feel. It already feels so good but she really really wants him  _ inside _ .

He chuckles, slapping his dick down on her clit. It’s only a little painful but it’s wet and it sounds absolutely dirty. And she can’t lie — it’s such a turn on.

Dean presses his dick down on her clit, threads the underside back and forth through her slit until the head catches at the entrance of her cunt and she wriggles her hips, pushes it down because she wants to feel it inside. His breathing is ragged as he watches down to where their bodies connect.

Pausing, he looks her in the eyes, his brows knit together, “Condom?”

_ If _ she could think straight, she’d say  _ yes _ . But she’s incapable of thinking, the  _ lust  _ for him and the  _ need  _ for his cock is too overwhelming.

Instead of insisting, and for the lack of better judgment to tell him to wrap up his cock, she finds herself shaking her head, “I’m good if you are,” 

Y/N might not be thinking straight right in this moment, but she knows what she’s getting herself into. She still has her IUD. She hasn't slept with anyone since Jimmy and from what she gathered, Dean likes to have control over everything, it wouldn’t surprise her if he gets tested on a regular basis because he’s so much to lose. And besides, she trusts him. He wouldn’t endanger her. 

“Yeah,” It comes out a mumble and his eyes drift off from her face to where the tip of his cock rests inside on the opening. It’s just the tip but already that feels so fucking good. He doesn’t push in, nor is it pulling away. There’s an inner debate that's going on, which she can’t quite put a finger on, but then he trails his eyes back up to hers, mumbling again, “Okay,”

Dean’s holding her gaze as he slides in and she has to bite down on her lips as his dick stretches her. He’s going in agonizingly slow and she knows now why. He’s not exactly small and she’s not exactly used to the size of him. 

When he’s halfway inside, he drops his body down and braces himself on his forearms next to her face, caging her in. His hands stroking her hair on the top of her head back as he nuzzles his nose along her cheek.

“You okay?” He whispers soft, lips brushing against her skin. 

“Yeah,” She breathes out, “So full,” 

There’s a chuckle as he kisses her cheek, “I’m only halfway there,”

“Shit,”

“You want me to stop?” 

“No,” She shakes her head and he kisses her nose, “You can tell me to stop anytime, okay? I won’t be mad,”

“Dean?”

“Yeah?”

“Fuck me,”

He laughs, the sound sharp and loud. It’s something she’s not used to too, the playfulness when having sex. It feels so natural with him. He kisses the corner of her mouth as he pushes himself in another inch.

“Christ, so tight,” He hisses under his breath, “Doing so good, baby,” He coos as he kisses her to distract from how wide his dick is stretching her cunt, “So good for me,”

She can’t help but clench down at his praises. Praise kink, something she never knew existed before Dean but now she just can’t get enough of it. 

“Fuck,” He drops his forehead down to hers, “Don’t do that,”

Chuckling, she circles her arms around his neck and Dean works his way down her face, plants little kisses while he pushes himself further inside. He’s being considerate and checks on her constantly. It almost makes her feel like this is what they are. Like this is not just a fuck because it’s convenient. Almost makes her think that he feels the same way as she does.

They both moan out simultaneously when he’s sheathed. He pushes forward some more, and it reaches her so fucking deep. 

Dean pauses to give her time to adjust, pecks her lips, his nose brushes hers, “You okay?” 

Y/N can’t answer in words, but she hums her approval. 

“Good,” Dean hums back, teeth nibbling down her throat, “God, you feel so fucking good like I knew you would. Stretching wide for my cock, such a good girl,”

She clenches again. How can she not when he says these dirty things that make her tingle?

“Fuck, you’re killing me,” He chuckles, drawing his cock back only to fuck right back in, eliciting a drawn out moan from her.

He slowly peels her hand away from his neck and pins them above her head, holding them there with only one of his hands while his other hand goes to her waist. It squeezes at her flesh, fingertips digging into her skin. He kisses her, slow and deep, his tongue replicating how he’s fucking her. 

“God, you’re so deep,” She moans against his temple as he kisses her jaw and moves further down to her throat. 

Dean sucks skin into his mouth and mumbles, “Too deep?”

“No,” She smiles, “Go deeper,”

“Jesus,”

He picks up his pace, presses his pelvis closer, tries to go deeper with every thrust of his hips. It’s slow and dirty, it’s not like she thought it would be with Dean but maybe he just really wants to take it slow the first time.

“Look at you,” He growls, pulls at the skin on her throat, “Taking my cock so well, baby,”

“Mmmh,”

Dean lets go of her hands as he pushes himself up. He pushes his knees under her thighs, her ass is hanging off his thighs as he begins to fuck her a little faster, a little rougher too, still pushing himself in as far as he can go with every thrust. 

Her fingers fists in the sheets as his hand travels all over her body, fingers pinching and pulling at each of her nipples, hands kneading and squeezing her tits. Sometimes so hard that it hurts but that’s a first too. She came to like the pain. 

This is a completely new angle. One she hasn’t experienced before. His dick not only hits her deep but also so fucking right. The approaching orgasm is winding up in her belly. 

“Fuck,” Dean groans out, “You’re close, yeah? I can feel you. The clench of your pussy is unreal,” 

Instead of waiting for her answer — not that she can answer him anyway from the way she’s so fucking close — his hand goes to her cunt, thumb rubbing gentle circles on her clit. It’s really not fair that he can make her come with a flicker of his thumb. It seems like it’s way too easy, and yet, it does push her over the edge. 

“You’re coming on my cock! Fuck! Yeah, just like that, Y/N, feels so fucking amazing,” His breathing gets ragged and she’s still coming on his fucking dick but Dean fucks her through it, not letting her recover, “I’m going to come, too, fuck, your pussy’s just too good.”

“Come inside. I want you to come inside my pussy,” She doesn’t really know why she says what she says. Blame it on the high she’s on. Blame it on Dean. 

“What?” His brows that were already knit together knit themselves some more, “You—, fuck—,”

Y/N can see that he’s fighting to pull out but as soon as she says those words, it’s probably already too late, even for someone who’s always in control. 

Dean’s hands' grip firm around her thigh, blunt nails digging into her flesh as he pushes himself deep, spilling his cum inside her cunt with a low grunt that sounds absolutely sexy. It’s something she definitely wants to hear more of.

He drops himself down, cages her head between his forearms and starts to kiss her while he still thrusts his hips in and out of her lazily. Dean buries his face into the crook of her neck, kisses her there, his beard pricking her skin. He chuckles when he catches his breath, “You can’t say shit like that and expect me to have control over my cock,”

She giggles, her arms around his neck, fingers stroking the short hair there. He lifts his head to look at her. Sweats bead on his forehead and his nose, freckles and litters his cheeks. He looks so pretty, fucked out, and glowing. 

With a peck to her forehead, he winds himself out of her grip and sits back on his knees. His dick comes out with a wet squelching sound, making her flinch and she whines because of the loss. 

Dean threads his finger through her slick slit, watches as his cum runs out of her pussy, wetting the sheets. He pushes two fingers inside and she flinches because she’s so sensitive. She hears the cum sloshing inside as Dean moves his fingers around inside.

“I never came inside someone without a condom before,” He says truthfully and his eyes aren't really leaving her pussy. He seems too mesmerized by it, and he apparently likes what he sees because there’s another groan escaping his lips as another blotch of his cum runs out.

“No?”

“Nah,”

He lays down next to her and makes her lay her head on his shoulder. Dean pushes his still cum slick fingers to his mouth, wraps his lips around it and has a taste of both their combined cum. It’s totally dirty not to mention absolutely filthy.

“You’re so filthy,” She chuckles and Dean grins before he places the fingers to her lips. She parts her lips too easily, letting him push his fingers into her mouth, lets him draw patterns with their cum on her tongue, lets him fuck her mouth with his thick digits. 

“I guess we’ve now established that we’re both fucking filthy,” He chuckles.

Dean replaces his fingers with his tongue as he kisses her deep and rough, sucks their tastes off her tongue.

  
  
  
  


*

  
  
  


They take a shower, and he fucks her against the glass shower wall with her legs around his waist, her hands pinned above her head while he spreads kisses all over her face and throat. It seems like she can’t get enough of him and he has a hard time resisting either.

“That defies the purpose of a shower to clean up,” She jokes as she stands in front of the sink with a towel wrapped around her body while they both brush their teeth.

He has a towel slung low on his hips, and looks stupidly cute with his damp hair and the boyish grin he sends her from behind his toothbrush. Their eyes meet in the reflection of the mirror. 

Dean walks closer and spits into the sink, rinses his brush, and puts it back in the holder. She found her brush in the holder too when she walked into the bathroom, and was surprised that he didn’t throw it out.

Lowering his face to her shoulder, he presses a kiss on her skin, his beard prickles, “You’re just too hard to resist,”

She feels the blood rushing to her face and Dean winks before he walks out and leaves her to finish.

Walking out, she finds him already in bed, the sheets pulled up to his stomach as he checks his phone. She makes her way to her dress that’s now draped over a chair and is about to step in when Dean lays his phone onto his nightstand and pushes himself on his elbows.

He sends her a frown. “What are you doing?”

“I, uh,” She starts to say, “Just thought I should leave,”

“Why?”

Y/N doesn’t answer. 

Dean threads his hand through his damp hair before he drops it on the bed, “Is it because of Missouri bringing in coffee in the morning? I already told her not to bother.”

“What?”

“Yeah, so you wouldn’t get woken up,”

“Dean,” She starts to say, and then she stops. Doesn’t know what to add to what she started. Not really. She thought he wouldn’t want her to stay. Especially now that they were so intimate with each other. She can imagine that Dean was the kind of guy who needs his space after sex.

Dean sighs when he sees her hesitation, “Look, I’d like for you to stay, okay?”

To demonstrate, he lifts up the covers and pats at the space next to him. He’s wearing underwear. Thank god. It’s stupid but she wouldn’t know if she could sleep next to him without that barrier between them. It’s for her own safety. Maybe his too, because she’d probably pounce on him like a bitch in heat sometime in the night.

“You sure?” 

There’s a chuckle, “Never been more sure of anything in my life,”

“‘K,” She nods and walks over, climbs in next to him. And suddenly, she remembers the reason she wanted to go back to her room for, “But Liv,”

“Right,” Dean rolls himself away from her and out of bed. 

Has she said something wrong? He sounds like he’s pissed. Apparently talking about her child is a dealbreaker for Dean. That’s good to know. She can’t say that she’s not disappointed.

Y/N gets out as well, still naked and Dean’s standing by his dresser, gets his worn shirt from tonight out of his hamper. 

“Are you going out?” She asks, and she doesn’t want it to come out sounding like she’s disappointed but it probably did.

“No,” He chuckles as he strolls over and holds it out for her to wear, he waits until she pushes her arms through the too big shirt, buttons it up with while he smirks, “We’re sleeping in your room so that you’re closer if Liv should need you,”

_ Oh. _

“Why do I need to wear a shirt?”

“If you wanna walk through the house naked, be my guest.” He shrugs, “But tell you the truth? I quite like seeing you in my clothes.”

He walks back to the dresser and pulls a t-shirt over his head, grabbing his phone before they make their way to her room, her hand in his. 

**Notes for the Chapter:**

> So, I have decided that I'm going to post three times a week. You'll get the chapters on Monday, Wednesday and Friday, yay?   
> Also because I'm already working on my next series and I'm excited to share it.


	19. Chapter 19

Y/N’s sitting in the living room, surrounded by dresses. Wedding dresses, and dresses for the rehearsal dinner.  _ Oh god, _ so many dresses. Rowena is sitting on the other end of the couch and Pamela is sorting through even more on the rack she used to roll them into the penthouse. 

“Do we have to have a rehearsal dinner?” She throws the question in the air, aimed at no one in particular, as she leans back, sinking deeper into the comfort of the couch, already so so done with the whole wedding. It’s not even a real one.

“Oh, honey,” Rowena says in a mixture of sympathy and pity but afterward, her lips stretched wide on her neatly made up face. Y/N swears, the woman must be a witch or something because she always manages to look so flawless and she’s always able to keep a clear head, acts like nothing can stress her out. She guesses, it must come with the territory of working for Dean fucking Winchester. He’s probably not the easiest one to handle, but Rowena apparently does a bang up job with it, “You sound like Dean. He asked me the same this morning,” Rowena looks at her pout and the pleading glint in Y/N’s eyes, “And I think he had the same expression as he sank into the couch in his office.”

That’s brand new information. Like, she didn’t think Dean would be opposed to it. Everything to keep up the illusion, right?

The red haired woman smiles reassuringly at her, “You actually don’t have to, but take my advice. You don’t want to meet the people on the wedding day. It’s better to at least get the tension out, get to see all the faces of the snobs who do not care about you anyway. And you know what? If you deal with them at the rehearsal dinner, you can avoid talking to them for too long at your wedding.” The woman raises one of her eyebrows, and Y/N is somehow convinced that Rowena is absolutely right.

“But it’s another night of mind numbing conversation about their new yachts and what not,”

Right now, she probably sounds like a teenager, but she can’t bring herself to care. 

“You sweet summer child,” Rowena mocks in a playful tone of voice, “That’s what you’re marrying into. Get used to it. They don’t really care about deep conversation, you know? They just want to talk about their success and talk you down whenever they get the chance because you’re not one of them. Time to put on that thick skin of yours, darling.”

Thick skin? Y/N agrees that she has one because of what she’s gone through as a young mom with a partner who hardly cared, but she thought she’s going to be able to leave that thick skin of hers behind at some point. Maybe one day..

While Rowena and Pamela are talking about the wedding bouquet, because God forbid the colors won’t match her dress, the chef comes in and starts to prepare their lunch. She almost feels bad that they are hogging the whole living room, leaving the staff to have to retreat even though they insisted that it was okay. Missouri made sure that it was really okay because, after lunch, she joined them too, bringing them a bottle of Champagne while she sat down and telling Y/N not to tell Dean that she’s looking at wedding dresses while she should be working. 

“Your secret’s safe with me,” Y/N answers the woman, a playful smirk tugging at the corner of her lips.

“And yours with me,” Missouri winks at her to which Y/N has to frown because she can’t really put a finger on what the woman means by that. 

Missouri doesn’t elaborate, but instead, she starts to talk to the other women and gush about the dresses. Yeah, they are pretty, Y/N can’t deny that, but they are somehow  _ too  _ pretty, if that makes sense. Like, she knows that Pamela tries to find a dress for her that suits her but somehow it just doesn’t  _ feel  _ right. And then again, when she feels like this, she has to remind herself that it’s technically  _ not  _ her real wedding, that she’s a piece in a game. The problem is more that it’s probably the only wedding she’ll ever get in her life, so her feelings are actually all over the place because she somehow wants it to be good, despite it being a sham.

After downing three glasses of bubbly to get her in the right mood to look at and trying on more dresses, Y/N excused herself to the bathroom and when she’s walking back, she quickly forgets to pull herself together. She’s still a little sore from last night and it shows in the way she walks.

“Why are you walking like that, dear?” Rowena’s the first one who notices. Of course she would.

Y/N bites the inside of her cheek, stands up straighter to conceal the weird posture and especially the waddle she has going on.

Rowena sends a knowing look to Missouri and the other woman just giggles softly to herself. 

Rolling her eyes, Y/N sits down with a grunt, and is happy to realize that Missouri has brought out water as well so she takes a glass, sipping on it because she doesn’t think she should drink more of the bubbly as prevention not to end up being a sobbing mess and pour her heart out to women she barely knows.

Bobby came home after she’s gone over her dress and she’s happy that the women have found another victim to play around with. So she sits back on the couch and zones out while they pick on Bobby, hoping that nobody will notice her zoning her mind out of the conversation for a little while.

Zoning out also means that she recalls the memories of last night and this morning. 

Y/N fell asleep right after they settled into her bed and the next thing she knew, she woke up to the sounds of an alarm and noticed that she was still tangled in the sheets with Dean. His arms were around her body and he pulled her into him a little tighter when he realized that she had woken up. He breathed down her neck, and kissed her behind her ear. 

“This is ridiculous! I look ridiculous!” Bobby came back into the room wearing a tux that the women told him to go try on. The sound of his shouting brings her back to reality. 

Pamela is dancing around him, pulling at the tux and straightening it out before taking measurements to amend it. Y/N can see that he looks uncomfortable. Bobby is a guy who owns exactly one black suit which he uses for every occasion. 

“You look great, Bobby,” Y/N says with a smile, hoping her words will calm the old man down a little. 

“Yeah?”

“Yeah,” She confirms, “You’ll look great walking me down the aisle.”

The look Bobby sends her is laced with sadness. She recognizes it when she sees it. He probably feels the same sadness she feels. Probably wishing he would one day walk her down a real aisle to her real wedding. But since that’s definitely not in the cards for her, they will have to make do with this one. 

“You  _ will  _ walk me down the aisle, won’t you?” She asks, a little unsure. They haven’t talked about it because, for her, it’s a given that he would do it. 

Bobby sends her another look, this time his eyes have softened, “Sweetheart, I would walk through fire to be there for you, you know that.”

She blinks away the tears, tries not to break down from all the pressure and the feelings that she bottled up inside, and she nods at Bobby before she looks away. She just had to, otherwise, she would start crying like a baby.

Pamela seems to sense the tension so she changes the subject, “Your maid of honor will be here later, right?”

“Huh,” Y/N turns her head back to look at Pamela who’s still righting something at the front of Bobby’s tux, “Yeah, Donna said she’ll come up in the afternoon. Apparently, Dean gave her some time off.”

“Ah, what a nice gesture,” Pamela adds. 

It is, she reckons. He’s really trying, and Y/N can’t help to think that she’s actually very lucky to get to marry him. Still, she can’t help being a little sad about it too. Maybe because she wants it to be real? Maybe because she knows that it’ll end and she’s going to come out of it with a broken heart. But also, when she thinks of it, maybe it’s better this way. Perhaps it’ll be easier to deal with the heartbreak and loss when she knows that it’s something that’s bound to happen. That way she can prepare herself for the fall. 

She shakes her head to clear it from those thoughts, though. There’s no good coming out of it if she lets them occupy her mind. No, she decides, she’s going to try to enjoy this thing while it lasts. She should, because that’s the thing Bobby and Donna both have told her to do and honestly, she really does. Sex with Dean is so much better than she thought it would be. She was afraid that it’d be all weird and tense, but it’s the complete opposite, and it leaves her wanting more of it. Dean’s so damn addictive. 

  
  
  


_______________________________________________________

  
  
  
  


Dean slums into his chair in the meeting and rubs a hand over his face. It’s the sixth one today and he’s tired. The only good thing about this meeting is that he doesn’t have to speak and can just listen.

While Frank is presenting and talking in the front of the room, Dean can’t help but let his mind drift off, which is so not him because usually he wants to know everything. This comes with his urge to have control, but today, he can’t really find it himself to care.

Instead, he lets his mind wander to last night and this morning and he starts to smirk. 

His alarm went off way too early for his liking. He doesn’t know if he’s somehow not used to going to bed too late anymore or if it was the girl next to him that makes it harder for him to get up.  _ Maybe it’s both _ , he thinks, trying to bury the feeling that he also thinks the girl involved has more to do with it than his age. 

After his alarm went off, Dean let himself float in the state of contentment and coziness of their limbs tangled together in her sheets a while longer. That move was uncharacteristic of him too. Usually, he gets up and gets going, preparing himself mentally for the day ahead but this morning, he found himself preparing mentally for the moment that he had to get out of bed. 

While he was certain that he should part from her, he found himself holding her a little tighter, pulling her into him and burying his face deeper into her neck to inhale her scent. She partly smelled like him because they showered in his bathroom and she wore his shirt to bed. Evidently, he found the fact that she smelled like him very pleasing because he was growing hard and that was when he knew that he had to get out because if he didn’t, he would never get anything done. 

Dean slipped out with a kiss to her temple while she was still dozing. It took all of his self control not to crawl back in there and lay himself beside her. Instead, he retreated back to his room to take a cold shower to wake up and calm himself down.

Rowena came into his office in the morning with his coffee, found him pacing around because his mind was all over the place. Dean knows he’s not a fucking good man. If he was a better man, he would have gone into the bathroom last night, and would have put on that damn condom, even if she said it was okay. He’s not a good man because he let himself go this far. Coming inside of her the first time was pure accident. He could barely hold himself together and then she had to go and spill those dirty words that hit him in all the right places. Coming inside her the second time should have been a coincidence but it felt more like a pattern to him. Fucking someone bare without the barrier of a condom should not be the norm, nor should it be standard for him, but now that he’s gotten a taste of it, he can’t really think of doing it any differently. Besides, they’re getting married and Dean’s determined to make it work, so at least there’s that, right? Right.  _ Jesus _ , he’s so screwed.

Miraculously, while Dean was still deep in his thoughts, the meeting somehow ended without him even noticing. 

He slips out of the room, instructing Frank to send him the presentation so he can look over it again when things calm down. He will have to, he knows, because it’s his own fault he didn’t pay attention. It will be another hour of his time where he could do something else. Or  _ someone  _ else, for that matter. Dean can’t help but smirk a little at his own dumb thought as he makes his way to his office.

Dean sinks into his office chair and boots up his computer to clear some other meetings for tomorrow which he didn’t have time for. He knows that he could just tell Rowena to do it for him but she’s not supposed to know it either so he’d rather do it himself. He still has time to kill until Sam gets here after all. 

The email square pops up on his screen, telling him that Frank has sent over his presentation but Dean figures that if he didn’t care to listen to it before, he sure as hell won’t be able to click through it now. Not when his mind is occupied by something else entirely. He should get a fucking grip because he knows that he can’t keep on living like this. After the wedding, everything will get back to normal, meaning his head will hopefully be free of stress, so what if he takes the liberty to bask in the good feeling for a couple of days? Perhaps he even deserves it.

It’s not even ten minutes later when there’s a knock at his door. Frowning, Dean eyes the bottom right corner of his screen to check the time. It definitely isn’t Sam. Sam wouldn’t bother to knock. He still has his schedule open and doesn’t see anything that’s supposed to be happening now. 

Clearing his throat, Dean calls out, “Come in,”

Rowena opens the door and Dean takes it that she finished going over the wedding preparations with Y/N upstairs. And then, he smiles, not because of Rowena but because of the little girl who let out a squeal when she sees him and climbs right up into his lap. 

“Hey princess, what are you doing here?” His eyes trail from the girl to Rowena who closes the door before she walks deeper into the room.

“Donna’s up there and I thought I could bring her down as a change of scenery until the girls are finished.”

“You know she shouldn’t be here, right?” Dean asks Rowena as the little girl starts to play with the keyboard and the mouse on his desk. 

“Why shouldn’t I be here?” Liv turns her head back from the screen to stare at him, her eyes narrow. It’s totally cute and almost makes him forget that he said something he maybe shouldn’t have.

“Heeeeeeey,” Dean jumps in to save himself and to conceal the awkward situation, “You wanna watch some videos, yeah?” Quickly, he types in the youtube address into the search bar of his chrome and then he types in  _ tangled songs _ . That should keep her occupied for a while.

Dean lifts the little girl up and lets her make herself comfortable on his office chair as he walks over to where Rowena is standing, “So, you know that it’s a risk, right?” 

“Relax,” Rowena smiles when she’s watching Olivia sing along to the songs that are coming out of his computer, “I told everyone who asked that she was my niece.”

“Oh, right, yeah, sure.” Dean rolls his eyes.

“Didn’t I tell you to relax?” Rowena laughs, “I asked Y/N, by the way. She said it was alright as long as I always have an eye on her.”

“Will you?” Dean raises his eyebrow, knowing the answer before Rowena even opens her mouth.

“Well, I have to make some phone calls but I won’t be long,” 

Dean sighs.

The woman glares at him. Dean can see it out of the corner of his eye, “Care to tell me why we have to keep her a secret and for how long?”

He pushes his hands into his pant pockets and shrugs, “Y/N said she doesn’t want her involved.”

“Understandable.” 

“Yeah.”

“But,” The red haired woman turns to him, “You are getting married. It’s getting as serious as it can get. I think you have to show her to the world at some point. You know that they will find out sooner or later,” 

“I know,” Dean mumbles, “I just don’t know if that’s really the only reason. I feel like there’s something she doesn’t want to tell me.”

“Oh dear,” Rowena scoffs.

“What?” 

“You’re not even married and you’re already keeping secrets?”

“Look,” Dean says, “I don’t mind her having secrets. We’re not… you know,”

“Oh, Dean,”

“What?” This time it’s Dean’s turn to raise his eyebrows.

“Nothing. You kids are crazy.” Rowena shakes her head, “It’s just, I’ve worked for you since you took over and can I just say,” She trails off as she takes another look at Liv, “You’ve changed, Dean. You’re calmer nowadays.”

He doesn’t answer. Doesn’t know what to say to her revelations but before Rowena could make it awkward, she turns around and announces that she’s going to make some phone calls and will be back to collect Liv to go up again.

Dean can tell by Rowena’s look when she came back again a half hour later, that she was quite amused by what she saw.

He has converted his table by the couch into a drawing desk, had called for someone to get him coloring books and Liv has spent some time drawing and coloring things but now she’s sitting on the couch with a laptop propped on the table watching  _ The Boss Baby _ . 

The woman crosses her arms over her chest, “You wanna teach her to be a boss already?”

“Hey,” Dean chuckles, “She chose it.”

Little does Rowena know that Liv is already a boss.

  
  
  


*

  
  


The remainder of Olivia’s presence is still visible when Sam shows up. Sam chuckles as he sees the drawings and collects them off the couch to make room for him to sit down. 

“Liv?”

“Yeah,” Dean sits down in the chair opposite of the couch Sam’s on, “Rowena had to make some phone calls.”

“You really are soft for this girl, aren’t you?”

There’s a glint in Sam’s eyes and Dean doesn’t really know who he means by that. If it was Y/N or Olivia. But he reckons that it doesn’t really matter because the answer is basically the same, “Yeah,”

“I see,” Sam nods with a grin and proceeds to take out a manila folder which Dean assumes is the new extended contract, “Y/N told me yesterday that she’ll marry you for a payout, so you will only have to pay once and don’t have to keep paying her daily.”

Dean frowns, “She did?” Because this information is new to him.

“Yeah.” 

“How much?” Dean doesn’t know how he should feel about it. Maybe it’s disappointment. Just when he thought that she wouldn’t be one of those girls who just wanted money from him. But maybe he read her wrong all along. Perhaps, he has been played, he just couldn’t or rather don’t want to see it.

“I don’t think it’s nearly enough to cover the therapy that she’ll need by being married to you, but whatever she wants, right?” Sam grins broadly as he slides the contract over to Dean.

He picks it up, his hands shaking a little, but when he sees the sum, his eyebrows begin to rise on his forehead. 

“60k? Is she serious?”

Sam shrugs, “I guess she just wants college covered for when Liv one day decides to go to college. You know how expensive it is.”

“No, but seriously. She could have asked for millions but she wants this? She knows that I make this amount in less than a week and on a good day I make even more.”

“I told you that you chose good, Dean. She has no fucking interest whatsoever in what you could give her.”

_ Yeah _ , Dean thinks,  _ it’s because she wants what he’s not able to give _ .

“I don’t wanna sign it.” He says, “At least not without talking to her first.”

“I think you should sign it.” Sam interjects, “Come on, Dean. It’s for the best and if you want to give her more you are free to do that, but at least we have a contract and can move on from there.”

In his head, Dean knows that Sam’s right. In his heart, though, it doesn’t sound as right as it should.

He places the contract back down on the table, thinking that he’ll sign, but not now. Not yet. 

When Dean looks at Sam, Sam sends him a knowing look. “So, anyway,” His friend tries to change the subject, “Care to tell me who this Jimmy Novak fella is who is calling my office to demand to speak to you?”

“What?” The name doesn’t ring any bells at all.

“Yeah, apparently, he called here, but Rowena told him to get in contact with me.”

“What does he want?” Dean asks curiously. 

“He said he’s Olivia’s father.”

_ Oh.  _

Dean’s eyes grow wide. And then he frowns, “What does he want?”

Sam snorts, “What does he want? Obviously, he’s going to try to milk you since you’re going to marry his ex.”

His friend’s not an idiot, Dean knows that. And Sam’s probably right. Why else would her ex-boyfriend get in contact with him and especially now, when they’re about to get hitched. And from the way Sam looks away when Dean’s eyes meet his, Dean knows something’s up. “What is it?”

“You’re not going to pay him, are you?”

“It depends on what leverage he’s got.” 

“Olivia,” Sam answers flatly.

Dean’s jaw starts to tick, “Liv?”

“Look,” Sam uncrossed and recrossed his legs, “Apparently, it wasn’t a mutual split from his side. She took Liv and left. He’s determined to get her back.”

_ Shit. _

“That would break Y/N’s heart.” He mumbles under his breath.

“Look, I don’t know exactly what went down and maybe you should talk to her about it first.” His friend quickly says before Dean can grill him about it some more. 

Dean leans back in his seat and rubs a hand over his face, scratches at his what he now considers a beard. He thinks before he speaks, “You still have his details?” 

“Yeah,”

“Call him over, I wanna know what he wants. I’ll call my guy to dig around. Name’s Jimmy Novak, right? Tell him to hurry because I promised Liv that I’ll be home before she has to go to bed.”

Sam laughs. 

“What?” Dean asks, a little irritated.

“Nothing, just,” His friend recovers enough to go on, “Home. Never heard you used that term for your penthouse before.”

Dean’s silent. What Sam just said makes him think.

“What if he can’t make it?” Sam asks as he pulls out his phone.

“Tell him it’s his only chance. He should take it or leave it. I know he won’t let the opportunity slip away.” Now, Dean wasn’t really sure if Jimmy will come but he has the feeling that the guy will show up and when he does, Dean will be ahead and ready. 

Sam eyes him before he pushes a button on his phone. And as Dean predicted, Jimmy’s too eager to agree to meet them.

“So,” Dean grins at Sam, “Whip out your laptop. I need you to draft up a contract for me.”


	20. Chapter 20

Dean’s taken off his suit jacket and eased his tie on the way up to the penthouse. The meeting with Y/N’s ex ran longer than he thought it would and he had to text her that he’d be up later, begging her to please keep Liv awake because he promised and Dean’s not one to break promises. Especially not when they are made to a little girl. And suffice to say, what he gathers from the meeting is that he’s fucking glad she’s not involved with him anymore. What a fucking douche. He tries not to judge why she got together with him in the first place. At least Olivia seems to be the best thing that came out of that relationship.

As soon as Dean steps into the penthouse, he’s immediately attacked by Liv who jumped right at him and climbed him like a tree. He couldn’t stop laughing at the little girl’s determination to get on his shoulder without any help. Of course, Dean gives in, pushing her up a little higher so she can sit on his shoulders.

“You alright up there?” Dean asks, feeling her grabbing a fistful of his hair and yanking at it. 

“Ya!” Liv’s laugh echoes off the walls in the hallway.

Y/N’s standing there too, her arms crossed over her chest, and Dean can see that she’s trying to frown but the smile tugging at the corner of her lips gives everything away. Pulling herself together and tightening her voice, she scolds, “Liv, you shouldn’t attack Dean like that. Let him come home first.” 

_Home._ It has a nice ring to it.

“It’s okay,” He assures her, hands gripping around Liv’s leg to keep the girl from falling down.

“I’m sorry, she’s just been really looking forward to seeing you. She was happy to stay up and wait.”

“Y/N, really, it’s okay. I promised her. I’m sorry it took me so long. Something came up and I couldn’t leave when I planned to.”

“You don’t have to apologize. If anyone knows about unplanned things that come up when someone wants to leave, it’s me.” She chuckles lightly, but the smile on her face doesn’t quite reach her eyes.

Dean feels a little guilty hearing it. He wonders how many times she had to stay late because something unexpected came up. It happens to him more often than he cares to admit and he bets it wasn’t any different with her. He can’t help but wonder how many times she couldn’t make it home on time to tuck Liv in and read her bedtime stories. 

Yeah, Dean feels absolutely shitty about it, even though he knows he doesn’t have to. Other people do the same every day but those other people are not _her_. He doesn’t care about them. 

He balances Liv on his shoulder and takes a step further into the hall towards Y/N. One of his hands grabs at her waist, pulling her into him and kisses her temple, “I’ll go tuck Liv into bed and read her a story, okay?”

“You sure you can handle that?” The glint in her eyes is back as she teases him.

“Yeah,” He chuckles, “You have no idea what I can handle, sweetheart.” He replies smugly and Dean can’t help but grin because he can see the flush of her face.

Honestly, Dean’s been looking forward to tucking Liv in. The feelings he has for this little girl have snuck up on him and he’s not even mad about it. So, doing all these things? It’s not really a chore but a privilege. 

“Okay, I’m going to take a shower. I’m thinking of going out with some friends to clear my head,” She’s hesitant when she says it, like she’s afraid that he’ll object. It’s totally cute and Dean has to suppress his grin.

“Of course,” Dean tries to act normal, tries to push the image of her showering out of his head and asks, “Where are you going?”

It’s not like he’s in any way opposed to her going out — well, maybe he is a little, as he would have loved to have a quiet night in where he can talk to her, but seeing that him requesting it without any purpose of going out to feed her to the media, Dean knows that it’s not his place to tell her not to go — it’s more like if she needed a driver, he could call someone to drive her wherever she wants to go. In hindsight, he maybe should have phrased it differently, so he adds, “I didn’t mean—, you know, if you need a driver, I will call for him, not that I keep tabs on where you’re going, it’s just— you know, I—” 

_Jesus_ , he’s babbling. He usually does not babble.

The frown on her face evens out as laughter bubbles out of her mouth. 

“You’re cute,” She’s still laughing. 

It’s his turn to frown. Cute? That’s not really a term he likes to go by. 

Liv’s starting to get antsy on his shoulder and he has to hold her a little tighter so the little girl won’t fall down as he watches Y/N calming down from her giggles. 

When she calms down enough, she speaks, “I was actually wondering if you’d like to join me? It’s probably not up to your standards but it’s a place I like to go.”

The question surprises Dean, but also it makes his heart do a strange thing. 

“You sure about that?”

“Yeah,” She smiles, “Who knows, it might broaden your horizon, it’s definitely different than the places you usually go to.”

“Sounds great, I’m in,” It comes out fast, uncontrolled, his voice a little higher. He’s absolutely ashamed but when she smiles back brightly, Dean can’t really be bothered about it. 

“Great, I’ll see you later,”

“Yeah,”

Y/N kisses Liv good night, who’s still propped on his shoulder and Dean watches her go into her room. When the door closes, he returns his attention to the girl, “So, you’re ready for a bedtime story, princess?”

He doesn’t really get an answer to his question but he thinks the squeal of delight the girl let out sounds like a clear _yes_.

  
  
  


*

  
  
  


Dean closes the door to Olivia’s room quietly. The girl was so tired, he barely made it to the third page Sleeping Beauty story. When he turns to walk, he bumps into Bobby. The man’s on his way to the kitchen. Bobby doesn’t pay him much attention, instead, the man mutters something about a _stupid tux_ under his breath before he disappears. He wonders if the old man will ever really warm up to him. 

The door to Y/N’s room is closed and Dean stalls in front of it, thinks about knocking but then he remembers that she said she’ll take a shower and what if she decides to take a bath? He knows that he desperately wants to see her, wants to ask her about her day before they go out, wonders if she’s found a dress for the ceremony, if she has settled on the flower arrangements but he also rather not interrupt her. Perhaps he should just go to his room, shower the day off himself. Suddenly, he’s not so sure of going out with her anymore. Doesn’t know if she just asked him because he was there or if she genuinely wants him to go out with her. He said yes way too quickly, hadn’t thought it through. And now, he just feels like he should let her go alone and get a drink on his own, sit down in his study and let the day wind down.

With his jacket in hand and tie loosely around his neck, Dean shuffles his way to his room. On the way, he catches an unusual aroma for that time of the evening. It’s food and Dean can’t lie, it smells heavenly. His stomach starts to grumble. He didn’t even notice that he was hungry. Most of the time he isn’t because either he goes out for a business dinner or he works so late that he simply forgets to eat. The closer to the living room he gets, the aroma gets more intense, filling his nostrils and his lungs. His mouth starts to water.

He rounds the corner and stares into the open kitchen, surprised at what he finds there. 

Y/N’s standing at the stove, stirring something that smells absolutely as delicious as she looks. Looking up from the pan, her eyes meet his and she sends him a small smile. Dean grins back, and he can’t help but notice that she’s just wearing black jeans and a simple gray t-shirt, a denim jacket over it. The clothes are clearly from her own collection because they look too worn out to be from the boutique. Still, it manages to coax an intense fluttering of his heart out of him.

“I thought you might be hungry.” 

“You didn’t have to, you know?” He strides closer slowly, draping his jacket on the stool at the kitchen island and sits down on the other one. 

“I know, but I wanted to,” She says, and adds, “Besides, you probably need to eat something before we go out, you know, to counter the alcohol,”

He has to laugh at that and she scoops him up a bowl of mac’n’cheese. 

Smiling at him, she slides the bowl over the counter, “I hope you like it,” 

“Love it,” He nods before digging in. He doesn’t have to taste it to know that it’s good. And maybe, he didn’t even mean to compliment the dish only. When he looks up, she turns her face away but Dean didn’t miss the flush of her cheeks.

  
  
  


_______________________________________________________

  
  
  


“What do you want to drink?” Y/N asks as Dean munches away at his bite of food. It’s still hot and he’s struggling with it in his mouth, tries to leave it open while his eyes are getting glassy. He might not like to hear it if his look was anything to go by when she said it, but he’s really cute.

“A eer s fin,” He stutters, his mouth still full of hot macaroni which he still can’t swallow as it would probably burn his throat.

She does her best to suppress her laugh and nods instead while she walks over to the fridge to grab him a beer. Dean tries to say thank you but his words are jumbled with the food still in his mouth. Y/N can’t say that she doesn’t like that part about him. Etiquette be damned, Dean doesn’t really care except when he's out in the open and has to socialize with people. She’s come to realize that he’s definitely not as stuck up as she thought he would be. He’s passionate about his work, he’s proud of what he’s achieved and he wants to maintain his success. She really can’t blame him for that. 

“You’re not hungry?” He asks as he finally manages to swallow the mouthful of mac’n’cheese and cool his throat with the beer.

“I already ate with Liv,” 

“Right,” He says and scoops up another spoon but he stops to speak before he pops the spoon into his mouth, “I’ll try to be on time from now on, okay?” 

“For what?” 

“For dinner,”

_Oh._

Y/N smiles, “Yeah, that’d be nice. But..” She trails off, “..it’s not that you have to.”

“I know,” He smirks, “I want to.”

Dean continues to eat as he questions her about her day, and it seems like he’s genuinely interested in knowing if she was okay with the location, the dresses, and just _everything_. He still has his tie hanging around his neck loosely. His shirt is folded back to his elbows, showing his forearms. Those damn forearms. It shouldn’t turn her on that much. It’s nothing special, right? But ugh, those forearms. Why are they so sexy?

She’s jolted out of her daydream when he asks for a second serving, and she can’t help to feel a little proud that he likes her cooking that much. 

Their interaction is simple throughout the meal but it’s not necessarily boring or bad. On the contrary, she thinks she’s falling just a little farther down the rabbit hole that is Dean, but she’s so afraid of what she’ll find once she falls down far enough to reach the bottom.

“Hey,” Dean’s voice jerks her back from yet another time she zoned out. She should definitely stop doing that.

“Huh?”

“I asked you if we still have time for me to take a shower,” He has one eyebrow raised, an easy smirk playing along his lips. He definitely knows what took over her attention because her eyes are still on his forearms which he now flexes. The little shit.

Dean chuckles and flexes his arm muscles one more time before he pushes himself off the island. By now, she’s trying to look anywhere else but at his forearms. It doesn’t help that the shirt he’s wearing stretches out perfectly tight around his chest, so she averts her eyes from him completely, takes the pan and his bowl and begins to clean up. 

“You still know that you don’t need to clean up, right?” He jerks his head to the pan. 

“Let me help around here, okay? You should go get ready.”

“K,” He mumbles, knowing that there’s no way that he can talk her out of cleaning up after herself — or him, for that matter, as he walks away from the island. Y/N wants to do it, and she can see that he’s slowly learning to accept it. “Do I need to dress up?” He turns around to ask before he rounds up the corner on the way to his room.

“No, look at how I’m dressed,” Standing back, she looks down at herself, sees that her jeans have a little hole at the knee that she definitely doesn’t think was there the last time she wore them. 

He smiles, “You know, it’s a shame you already showered, I was about to ask if you’d want to join me.” 

Her eyes widen and her mouth opens, gasping lightly as she tries to find her footing. She’s not used to someone being so brisk and that’s certainly something she still has to get used to when he’s around Dean. 

Before she can answer, though, he’s already gone but his laugh still rumbles deep and echoes off the walls.

  
  
  


*

  
  


Dean has dressed down, wearing worn out black jeans that hug the curve of his ass incredibly well. Not that she’s been looking. He also wears a simple black t-shirt with a plaid shirt on top, buttons open, and to shield himself from knowing eyes, he places a baseball cap on his head.

When he notices her staring at his cap his lips curve up into a grin, “Not that I don’t want to be seen, but I don’t want to draw unnecessary attention,”

“Right,” She smirks. He probably thinks she’s offended.

“It’s true,” 

“Yeah, sure.” 

She can’t help with the biting remarks and honestly wonders if he’s telling her the truth. Maybe he is. God knows she needs to somehow be able to go somewhere without all eyes on her and perhaps he’s been considerate, giving that he joins her and that people would recognize him first, even if he’s dressed like this. 

Dean decides to ignore her attitude, and fishes his phone out of his pants that are really tight around his hips. Not that she notices. “I’ll call the driver.”

“Dean no,” She shakes her head, “I’ve requested an Uber,” 

“Uber?”

“You know,” She shrugs, “Cars and drivers who drive you around?”

He frowns, “I know what an Uber is, Y/N, but I don’t know why we need one when I have not one but two drivers on my payroll.”

“Dean, relax, it’s gonna be fine.” She already takes out the phone from her purse as they walk to the door.

Dean’s still looking at her and cringes his nose, “You do that often?”

“Every now and then when I can’t be bothered taking the subway, yeah. Why?” She breaks from the open door to dash to the guest living room, telling Bobby that they’re on the way out. Bobby grumbles something that sounds a lot like _“have fun”_ but he doesn’t look up from the TV. 

Standing by the door, Dean watches her as she joins him, “It’s just,” He starts to say and stops himself before he inhales and starts to talk again, “You ride an Uber with Liv?”

“It happens sometimes, yeah,” Walking over to the elevator, they get in.

Dean leans his broad frame against the wall and sighs. There’s something about how he acts that makes her think that he’s not entirely happy with this whole Uber thing.

She looks up at him from the other wall, “What is it?”

“Nothing,” He shakes his head and looks away. 

Y/N doesn’t believe him.

  
  
  


*

  
  
  


Harvelle’s Roadhouse is bustling with people, even in the middle of the week. It must have something to do with the atmosphere. It’s just overall cozy, even if the inside is a little dark. But maybe that’s the whole appeal of it. People don’t come here to be seen. It’s the polar opposite of the parties she attended the last two weeks. 

The bar has a wooden floor, with a jukebox in one corner, pool table and darts in the other. It smells like stale beer as soon as one sets foot in, and yet, still, it’s somewhere she actually _likes_ to be, although that doesn’t happen a lot since she has Olivia, but once every blue moon, she’d like to let loose. Her friends meet up every week, and they seem to be ecstatic whenever she can make time to join them too. 

Dean gets out after her and he was right, with the get up, and especially with his baseball cap, not a single camera flash lit up on their way from the building to the waiting Uber, whereas normally there would be photographers waiting in the bushes to capture Dean. It could also be, though, that they’re already tired of him as he’s going to be off the market soon.

Y/N almost feels bad to have reacted as she did earlier.

Reaching out, she offers him her hand, perhaps also as a gesture of understanding. She hopes he knows what she means.

He nods as he threads his fingers through hers. His thumb rubs soothing circles on her skin as he looks ahead at the bar. Laughter and music spill out into the street of the cool night. “You come here often?”

“Not as often as I’d like to,” She offers him a smile, “You know, with Liv and all,” 

“Yeah, I understand,” He jerks his chin towards the bar, “So, what do I need to know about your friends?”

Walking over to the entrance, she pulls him with her. His hands are a little sweaty and if she didn’t know better, she’d think that he’s nervous but that can’t be, right? Dean’s never nervous. At least she doesn’t think he can be. 

“They are great. You know Donna,”

He nods.

“And you know Jody and Ash, because they both work for you.” She adds, as they squeeze past the people standing by the door who are smoking cigarettes. Dean suddenly tugs at her hand and pulls her behind him before he takes his hand out of her grip and instead, places it around her waist, pulling her closer as the big bearded guy by the door looks her up and down. She’s seen the man before but apart from staring, he’s not really been doing anything, so she’s not worried about him. 

“Ash?” Dean asks as he walks in with her, deciding to ignore the man himself.

“Yeah, Ash Lindberg?” Y/N looks up to meet his eyes, sees him frowning as he tries to connect the dots in his brain. 

“Oh, my IT guy!” He finally says when the coin drops, smiling broadly afterward, “I like him. A bit crazy but has the best ideas. And where does Jody work?” 

“PR.” 

“I don’t think I’ve ever met her in person.” Dean shakes his head and they walk further into the bar, zig-zagging around the people standing around. 

Garth stands up from the booth they’re in and waves at them as soon as he spots the pair.

“And who’s that?” Dean asks as soon as he realizes that Garth is waving at them and she waves back. 

“That’s Garth, he’s Ash’s boyfriend. A really great guy.”

Dean pulls her close, places a kiss on her temple and whispers, “Well, you like them so I’m pretty sure that I’ll like them too.”

As soon as they reach the booth, Ash and Garth slide off and let Dean slide into it first then her. Ash goes and gets a pitcher of beer before he grabs a stool to sit at the head of the table. 

The first couple of minutes were awkward. Maybe because the majority of them work for Dean and she thinks Jody and Ash needed time to adjust to the fact that the big boss is sitting at a booth with them. Donna is the only one who’s already used to seeing Dean and is talking for all of them. But after the bumpy start, it gets better, perhaps it’s also because Dean pulls out money and gives it to Ash to go get a bottle of whiskey.

“I would go myself, but it's hard to get out,” He shrugs, which is actually true and Ash just seems too eager because he never says no to a good time. 

“So, boss,” Ash’s tone of voice starts to get a little slurred after a couple of glasses but that’s nothing. She knows that it needs more to knock him out. Tomorrow morning, he’ll be the first one on his office floor and ready to go as if he didn’t get wasted the night before. She still doesn’t know how he does it, and thinks that she should ask about his secret because she gets a headache from two pints of beer. “You okay if I come in later tomorrow?”

A round of chuckles erupts. Ash’s always so bold with liquid courage. 

“Uh,” Dean smacks his lips and takes a sip from his tumbler, “I can give you an hour to get your act together, Ash.”

“Cool,” Ash nods his head and hums a little, “But you know what would be cooler?”

Y/N knows where Ash wants to go and she’s just really watching this scene unfold before her eyes in amusement.

“I guess you’ll tell me?” Dean asks, a boyish smirk plays along his lips.

“Damn right, I will!” Ash smashes his fist on the table, almost spilling Jody’s beer.

Jody reacts and hits Ash over his head, “Ash, the boss gave you an hour, just be happy about it!”

“No, you know how hangovers are, an hour is not enough!” Ash protests.

Dean grins, “Would you rather I fire you? So at least then you’d have all the time in the world to cure your hangover, Ash.”

The other man winces and Y/N reaches over, places a hand on Dean’s thigh, squeezes it which prompts Dean to turn his head and look over to her, his eyebrows raised. Y/N shakes her head. He smiles broadly as he drapes an arm around her shoulder, pulling her into him and he places a kiss on her temple. She doesn’t look but she can feel the eyes of her friends on them.

“Okay,” Dean roars, “Two hours, not further negotiable.” 

Ash smashes his hand on the table again, “Thank you! I knew you were cool!”

“Cool as in icy?” He raises an eyebrow and she squeezes his thigh again. Dean ignores her.

Jody laughs, “You know about that, don’t you?”

Dean simply nods but his smile doesn’t falter.

Y/N sits upright a little, his arm drops from her shoulder and is now wedged between her waist and the booth as his fingers dig into her skin a little where her shirt has ridden up. She looks at him, sees him grinning. “You’re not that bad.”

“Well, thank you,” Dean replies with a teasing gleaming smirk, “That’s a great thing to hear from my fiancée.”

That’s right. She is. Sometimes she forgets and is thankful that Dean reminds her. Not that she wants to forget it but what they have seems to be so natural and sometimes the title of what they are escapes her. 

She leans her forehead down on his, their breathing mingle. Her one hand cups Dean around his face and when she kisses him, it’s soft and tender. By now there’s nothing for show anymore on her side. She’s done with that and maybe, there’s hope that if she shows him enough how much she’s already fallen for him, he will change his mind too. 

_And if he doesn’t?_ Her inner voice asks. Her mind is racing a mile a minute. Will she be able to live a married life with someone who doesn’t even love her? Will she be able to keep on loving someone without getting a little love in return? 

Before she can even let her mind wander there, Dean manages to scoop her up and manhandle her sideways into his lap while they are still kissing. He deepens the kiss and she’s so lost in it. How can she not be? His one hand roams her back while his other one is placed firmly on the back of her neck, drawing her in closer. She can feel him hardening underneath her ass. 

“Let’s go play pool,” Garth suggested, and she hears that Ash agrees to it, probably to give them some privacy.

Dean grins into the kiss and pulls back a little, his eyes don't leave hers when he calls out, “Yeah, have fun,” He’s quick to kiss her again after the words left his lips.

“Yeah, and we’re going to sway by the jukebox,” Donna pushes at Jody. Y/N can see out of the corner of her eyes that Jody’s eyes are transfixed on Dean and her but Donna’s quick to push at Jody to make room for Donna to be able to get out of the booth. The woman follows her friend with a sigh.

Dean pulls back again and this time when he smiles, his perfectly white teeth are showing, “Have fun!” 

Y/N starts to laugh but Dean’s lips cut off the sound that bubbles out of her. 

It’s easy, she thinks. It’s so easy to get lost in his kisses. Dean’s a damn good kisser and she curses him a little for it because surely, nobody can be this perfect, yet he’s not so far off. She decides to tease him, puts her weight down, moves her ass a little to the beat of the music coming out of the jukebox and Dean groans into the kiss, drives his teeth into her bottom lips, making her giggle.

He parts from her lips, with a careful nibble, his voice a deep mumble, “You shouldn’t start what you can’t finish, sweetheart,”

She weaves her arms around his neck, and kisses his cheek as she noses at his temple. “Who said I can’t finish?” Her whisper is meant to come out sounding seductive, she doesn’t really know if it worked but she’s not going to stay and find out because she’s moving away from him, hops from the booth to join the girls by the jukebox.

“Tease,” Dean calls playfully after her.

  
  
  


*

  
  
  


Garth is walking around with that bottle of whiskey because he’s too afraid of leaving that at their booth because the bar is getting more crowded as the evening wears on. And it was the right decision apparently, because Y/N can see from where she’s standing by the jukebox with the other girls that their vacant seats are now occupied with another group of friends that are drinking loudly. 

She sweeps her eyes across the packed bar. Either there are just too many people here or she’s not really used to being in a packed environment anymore, having been tucked away in a spacious penthouse for far too long. But then she sees him, joking with Ash, a cue stick in hand. Dean seems to be listening to what Ash says but his eyes find hers as if on cue.

Has he been watching her this whole time or is that just a coincidence? She’d like to settle on her first thought, just because it makes her skin tingle pleasantly when she thinks that he’s watching her even when he’s playing pool, but she settles on the latter thought. Their eyes probably just searched out to check if the other one is still here at the same time. Nothing more than that. 

“I have to go to the restrooms,” Y/N shouts to Donna and Jody above the music and the chatter around them before she slides away from where they are standing and is making her way to the back of the bar where the restrooms are situated.

There are bodies swaying in her way, some girl almost trips and falls and she reaches out, helping steady them. When she almost reaches the door to the back that leads to the restrooms, a group of guys are blocking her way, deliberately leaving just enough space for her to squeeze through by brushing her body against two of the men. 

“Hey, baby,” One of them growls with a shit-eating grin. 

Instead of answering, she just squeezes past them, hoping and praying silently that he won’t touch her ass or doing anything else inappropriate. She knows those guys, has seen them on campus before, men who think they are so fucking slick. She wonders what on earth makes them think a girl would fall for such kind of behavior. They’re not in college, for fuck’s sake. Not that it worked there either, at least not for her. 

“Not up for a chat, huh?” The guy moves to close the gap further, “Let me buy you a drink, maybe that’ll get you talking,”

 _Yeah right_ , she thinks, that’s the only way they can get attention from a woman.

“Not interested,” Y/N grits her teeth and uses her elbows to push past them. 

“Bitch!” The guy huffs under his breath.

“Excuse me, what did you just call her?” A voice makes her turn around and look back. 

Dean’s standing there, his arms crossed over his chest. He’s making himself broader than the men standing around her. 

When none of them answers, Dean stretches out a hand and pushes the guy away, making more room for her to walk through and follows her back through the door. She takes a look back before walking through, sees Dean sending the other guy daggers with his gaze. It means that this is not over, she knows that much. She just hopes Dean can refrain from punching someone, as that would not end well, especially if they find out who he is.

He places a hand on the back of her neck, fingers spanning wide. They feel hot on her skin, “You okay?”

“Yeah,” She spins around, sending him an assuring smile, hoping it would calm him down should he still be angry, but she’s not prepared to see him already relaxed and calm while he looks down at her with that lopsided grin. 

“I’ll wait here,” Dean says and leans his back against the wall, crossing his arms over his chest again, looking much like a bouncer. 

She knows there’s no point in arguing, and besides, she really needs to pee, so she disappears into the restroom, leaving Dean outside. 

  
  
  


*

  
  
  


Pushing the door open with her elbows, she shakes her hands to get rid of the excess water because finding tissues to dry your hands in Harvelle’s Roadhouse is a rarity. She spots Dean still unmoved in his spot but this time his baseball cap is turned around on his head and she walks to stand in front of him. 

“All done?” He asks, his hands travel down her arms until they come to rest on her waist. 

“Yeah,” She smiles as she stands on her tiptoes to weave her arms around his neck.

Dean crouches down a little and she places a soft kiss on his lips. What she thought would just be a friendly peck, ends up being so much more because he’s quick to kiss her back, his arms wrapping around her tighter. Dean’s fucking quick, she has to give him that. Before she can even pull back from the kiss, he has them turned around, the cold wall hitting her back as he deepens the kiss before she gets the chance to break it.

He leaves his forehead on hers as he’s the one to break up for air and she starts to chuckle. 

“What?” He asks, still spreading kissing on her cheek, her nose, her lips. 

“Who would have thought that we were going to end up making out in the hall that leads up to restrooms in a shabby bar, huh?”

“Well, it’s a first time for everything, I guess,” The sound of his laughter joins her and he pecks her lips once more before he seals his warm mouth around hers and slides his tongue back in. He presses himself harder against her, the bulge poking at her abdomen. Her hands go down to the hem of his t-shirt, sneak their way under and Dean jerks back upon feeling her cold and damp hands against his skin, “Fuck,” 

She giggles, which prompts him to kiss her harder just to shut her up. Her hands go higher, fingertips trailing up his firm stomach, until she brushes against his nipple. It makes him shiver and he groans into the kiss. 

“I want you so bad,” It’s a low murmur, and he only breaks away long enough to say it before his lips are sealed back around her. 

Y/N sucks in his bottom lip and pulls back from his face before releasing it, “You wanna fuck me here?” 

Dean laughs, “It’s a night of firsts isn’t it?” 

She looks down to her toes, suddenly embarrassed but also so fucking turned on. She’s never done that before either, has never done more than making out with someone in public, maybe a little teasing and grinding. 

A girl pushes her way out of the women’s restrooms and joins the dude who went into the men’s but that’s not what she’s focussed on. There’s another door in the back, the handicap restroom which was built about two years ago when that was a requirement for the owner of the Roadhouse to be able to keep it open as a handful of guests had complained. 

“Come on,” She pushes past him and Dean doesn’t know what she’s talking about but he follows her nonetheless, her hand in his, pulling him along. 

  
  
  


_______________________________________________________

  
  
  
  


It’s cleaner than Dean thought it would be. As soon as they both step through the door, he kicks it closed with his boot and locks it up. She’s about to walk further in but he grabs her wrist and pulls her back, making her fall against him. He picks her up easily, walks her over to the generous wide sink and sets her down. Dean kisses her hungrily, the pent up feelings of her teasing making their way to the surface. His one hand sneaks up her front, cups her around her throat, while his other one moves up the inner of her clothed thigh until he cups at her pussy through the fabric of her jeans.

Arching her back, she keens and moans, seemingly wanting to feel him closer. Dean chuckles. It’s so easy with her, she’s so fucking responsive, he doesn’t want to fully admit that it’s the fucking best thing. 

He drops his face, sucks along her jaw and down her throat, his lips seal around her pulse point, sucks in her skin, “What do you want, baby. Tell me,” 

From the way she wriggles and pushes her hips into his palm, he knows what she wants, he’s just being an ass and wants to hear it out of her mouth. Because even though he told her that she can have him, it’s not really a guarantee that he can have her in return and he doesn’t want to overstep boundaries. Not even now when they are going to get married. 

“Dean,” 

Her voice comes out desperate and he absolutely loves how his name sounds bouncing off those sweet lips. Her hands grip around his neck, her nails rake down his clothed back. It makes him shiver.

“You want me to touch you, yeah?” He licks another trail up her throat, sucks at her earlobe. 

“No,” 

“No?” Dean pulls back a little, and is about to pull back for good but her hands are holding him in place.

“No,” Y/N repeats and he can see that she’s trying to suppress a grin that’s totally found a way on her face despite how hard she tries, “I want you to fuck me and you better hurry,” 

“Yes, ma’am,” Dea’s lips widen to a grin as relief washes over him. He claims her mouth again, pushes his tongue in deep, feels the vibrations of her moans on his tongue. 

His hands go to the button of her jeans, long fingers swiftly unbuttoning them and pulling them down past her ass. She helps him get rid of one leg, curling and uncurling it for him to push the fabric past it. She’s about to close them but Dean quickly knocks her leg open by her knee, kissing her again with a hunger he doesn’t even know he possesses as his hand sneaks up her thigh from her knee to cup her cunt through the soaked fabric of her lace panties. 

“Dean,” 

He chuckles and kisses her nose, “I like it when you say my name,”

There, he said it. It wasn’t even that hard to admit. 

“Fuck me,” 

“Yeah?” 

His hand is pushing the fabric of her panties out of the way, his finger dipping into her slick hole and soon adds another finger to it. There’s not going to be enough time to open her up thoroughly and she’s not really used to his size yet. He hopes that one day she’ll be able to take him without too much prep, he actually can’t fucking wait for that day to come where she could just take him whenever she wanted him. There will be no questions asked, because he’s always going to be down to fuck with her.

“Yeah,” She wriggles desperately, “Please?”

He definitely can’t resist when she begs. Dean growls before he kisses her again, his two fingers scissoring inside her tight cunt, “I fucking love it when you beg,”

“Yeah?” 

“Yeah,” His hand leaves her pussy, fingers making quick work on his belt and zipper. Taking out his cock from his underwear, Dean gives it some tugs, smearing her slick that’s still around his fingers on his shaft, goes in for a second serving around her pussy and coats his lengths before he guides the tip to her entrance.

“You ready, baby?” 

“Dean! Just f— oh my god,” Y/N’s moans out the last word, as he pushes in in one go, her eyes roll back and he’s torn between looking at her face and at the place where their bodies are connected. 

He kisses her to avert from the wide stretch he’s causing her, “You good?” 

“Shit—,” She swears and nods her head, “Yeah,” 

Dean draws back and reluctantly takes his eyes off her face to look at his dick that comes out of her pussy fucking gleaming. He groans lowly at the sight and pushes right back in, watches as her pussy lips hug his lengths when it disappears inside. 

After a couple more thrusts with his eyes trained on his dick fucking her wet pussy, he drops his face to hers, kisses her while he begins to fuck her harder, pushes himself inside so far, his balls are pressed hard against her ass. He leaves his forehead on hers, “You like when I go deep?” 

“Y— yeah,” She stutters, the fingers of one of her hands curl around the edge of the sink for purchase.

“Fuck,” Dean one hand is around the back of her neck as he pulls her up a little to claim her mouth, sucks in her bottom lip and only releases it when his thrusts become faster, “Your pussy’s so fucking good, baby. I won’t last,”

It’s a shame really. He doesn’t know when’s the last time he came so quick. But it is a quickie after all and he knows that he won’t get a freaking medal for dragging it out. Still, he’s not going to come before she does. That’s just not something he does. 

“That’s good, because I want you to come,” She says breathlessly as she clenched around him for emphasis. 

_This fucking girl._

“Damn, Y/N, you can’t do shit like that,” He scolds her as he slows down his thrusts deliberately. One of his hands leaves her hips and travels down, fingers drawing circles on her clit, eliciting moans from her that he gladly swallows when he kisses her, “You’re going to come first,”

He begins to fuck her faster again, rubbing her clit to the same rhythm just as he knows she likes it. 

Her back arches and she pushes her pelvis down, meeting his thrust, the nails of her hand on his biceps dig into this muscle and the clenching is almost a constant. It needs everything in him not to come before she does. 

“Are you going to come on my cock, pretty girl?” Dean growls low and that’s probably it. That’s the praise that will push her over the edge because instead of answering him, her eyes start to cross and her pussy pushes his cock out as she’s quivering around him. Such a pretty thing. _Fuck_ , he almost comes right then too.

“Dean,” 

His name leaves her mouth like a prayer as her face changes from a frown to the most pretty glowing smile he’s ever seen. 

“I got you,” He whispers and pushes right back inside, thrusting into the walls that are clenched together. It’s a tight fit but he makes it work, comes right inside while he’s holding on to the girl that’s falling apart because of him. 

  
  
  


*

  
  
  


They stay and clean themselves after. He really can’t get enough of seeing his cum dripping out of her. Wishes that he could take a picture, would probably make it his home screen, which he knows is totally creepy and a dick move.

Dean has his hand around her shoulder as they walk out into the bar. 

To Dean’s surprise, or actually lack of surprise, the annoying dudes are still standing there, blocking the way. The guys have recognized them and are elbowing each other. He hopes Y/N doesn’t look too bad that it could give away what they just did back there. Dean had made sure to help her with her hair and help make her look presentable again. He glances over and apart from the lips that are a little more swollen there’s nothing to indicate that they did some very naughty things back there.

“Look, the bitch is back!” One guy says and Dean doesn’t get the joke but the other one is laughing his ass off. 

He drops his hand from her shoulder and balls them into fists. She’s quick to grab his arm, strokes her hand up and down it, “Don’t listen to them, okay? We’re going home now.”

Dean purses his lips into a thin line and nods as he shoulders his way past them. 

“Oh, sorry, bitch is probably a wrong word. Whore is much better!” The guy calls out mockingly and that’s when Dean loses it.

He turns around swiftly, crowding the guy who’s a couple of inches shorter than him, “What did you just call her?”

The man doesn’t answer him, instead, he grins smugly, “You should put a dog tag on your whore man, or do you mind me going back there with her? I don’t mind sloppy seconds.”

Dean quickly grabs the guy around his throat, applies enough pressure to shut him up, grins equally smugly, the same way the man grinned to him before, “Say that again, I dare you!”

He wanted to wait but he didn't. Dean actually has never been a man of words, has always been better with actions. He punches the man right in his fugly face and then everything happens so fast. The guy who laughed before pounced on him and he ducks in time before Garth pushes the guy away from Dean and receives a punch to the jaw.

“Shit, Garth!” Dean wants to crouch down to see if Garth’s alright, but then Y/N pulls him up.

“Y/N, go! Get him out of here. We got this!” Jody shouts above the noises and the next thing Dean feels is Y/N’s hand around his as she pulls him out of the bar. She flags down a cab, pushing him inside forcefully once she gets the door open.

He’s slumped in his seat and she immediately takes his hand, the one that’s still hurting slightly because Dean definitely didn’t go easy on the guy, her fingers stroking it. Dean flinches. 

“You’re an idiot,” She huffs out but she doesn’t let go of his hand. 

“I just couldn’t let him talk like that,” 

“I know, but still, you’re an idiot,”

Dean chuckles. The next thing he sees is her face as she places a kiss on his cheek. 

The sound of her phone breaks the moment and she fishes it out of her purse, reading the words on there with a blank expression.

“What?” He asks curiously.

“Jody. She said security came and broke them off. The guys won’t be an issue anymore because everyone said they started it.”

“Good.”

“Garth has a broken nose.”

Dean flinches again, “Tell her that I’m going to cover whatever he needs.”

“I know you do but Dean, you can’t just go about punching people.” She scolds, “You should be glad Ash and Garth are so righteous and everyone knows that they have to protect you.”

“I’m sorry,” He doesn’t really know what to say and now when she lays it out like that, he can see that he’s really a dumb fuck in letting his feelings get the better of him. Maybe that’s the fucking reason why he doesn’t want them to surface. Feelings should stay where they are, and that means closed up in the bottom drawer in his heart. 

Y/N seems to notice his inner fight because the look she sends him almost breaks his heart. Damn those fucking feelings, seriously. 

She moves closer and Dean’s able to place his hand around her shoulder, “Were you ever in a bar fight in your life?” 

He has to chuckle at that. “No. I guess tonight’s the night of firsts, huh?”

  
  
  
  


*

  
  
  


Once inside, she goes straight for Liv’s room to check on her daughter while Dean shuffles away into his own room. He’s going to take a shower, wash off the guilt and shame for having caused trouble. It weighs heavy on him. 

While he stands under the spray, he thinks and is thankful for her friends that were there. He couldn't risk a scandal. Not now when the wedding’s right around the corner. It could affect everything. Dean closes his eyes as he lets the water rain down his back. He’s such a fucking idiot, he should have just walked away. Remarks like those never stopped him from walking away before when he had to keep up his reputation, and couldn't risk a stain on it. He doesn’t understand why it was so hard to do the same tonight. 

The shower should have calmed him down, should have helped stop his mind from spiraling, but it didn’t. Dean throws a shirt over himself and steps into his sweatpants, thinking of going to his study, grab another drink and sit on the couch, looking over the skyline to clear his mind but before he knows it, he stands in front of her door. His mind’s still going a hundred miles a minute. Too many thoughts to even get the right grip to sort them through.

He knocks twice before turning the knob and pushing the door open.

Y/N’s already in bed, the faint damp air of her own shower still lingers in the air. Dean takes it that she too, had to wash the dirt of the evening away. She didn’t draw the blinds, the lights from outside spilling in, bathing her in a soft and warm yellow glow. 

“Can’t sleep?” She turns her head around and whispers loud enough for him to hear.

Dean shakes his head, “No,”

Her hand pulls the comforter back next to her and Dean's feet take him there on their own. He gets out of his sweats and crawls into the bed, curling himself against her body as he settles. His arms go around her waist as he breathes against the back of her neck. It’s really hard to believe that the sheer presence of her calms him down. She grounds him. It’s only a matter of seconds until his heart rate slows down and Dean drifts off to sleep.

**Notes for the Chapter:**

> While I know that a lot of you were hoping for a showdown with Jimmy, I deliberately left that out because that’s not how the story was supposed to go. That’s not the story I was trying to tell. But you’ll get a glimpse of what has been talked about later.


	21. Chapter 21

**Summary for the Chapter:**

> Delicate subject ahead. Mention of physical abuse.

As Y/N’s eyes flutter open, she feels the dip of the mattress at her back. Squinting her eyes open a little, she braces herself for what’s to come, knows that dip too well, a weight that is barely there. And sure enough, a voice pierces through the silence of the morning.

“Mommy! Wake up!” 

Olivia climbs over her body, little limbs holding onto her, pulling and pushing until the girl straddles her stomach. The little girl’s still in her sleep attire herself. 

Turning her head, Y/N scans the room. 

Dean has already left, probably wanting to leave before Liv’s early morning attacks, maybe also because he wants to avoid the girl's questions. Her gaze returns to her daughter, the girl smiles a bright smile, the gap in her teeth slowly filling with a new tooth. 

“You wanna tell me why you’re so excited, hhm?” 

“Mommy,” Liv lays herself on top of Y/N, nuzzles her face into the crook of her mother’s neck, “Dean said we have to get dressed! He has a surprise for us!”

“Oh? Did he now?” 

She wonders what it could be and her mind already races. She can’t possibly go anywhere with Liv. Not when the things still aren’t settled with Jimmy. He’s not to know that they are here. But it makes her wonder why Jimmy’s been so quiet. Last she heard, he was about to expose her, and now that she thinks about it, she indeed hasn't heard from him for way too long. The silence is worrying her. It feels like the calm before the storm.

“I did.” 

The voice that pulls her back into the here and now comes from the door and she tilts her head to the side so fast she feels the kink in the back of her neck, and has to momentarily flinch. When she opens her eyes again, Dean’s standing there, in a simple black shirt and black jeans, a plaid dark green shirt over it. The color suits him. It brings out the color in his eyes. His beard looks good on him, and he has ditched the baseball cap. 

Liv’s quick to lurch from the bed with a squeal and runs towards Dean. His smile is broad when he lifts up the girl and twirls her around before he sets her down and kneels next to her.

“You go and get dressed, yeah? We want to leave after breakfast.” 

“Yay!” Liv bolts out of her room before Y/N can stop her.

Slowly sitting up, she leans her back against the headboard. Her mind’s still too foggy to even process what’s going on. 

Dean, meanwhile, walks to her closet, takes out the first pair of jeans and shirt he can find and lays them on the bed, “You should get dressed, breakfast is ready.”

“Dean, don’t you have to work? And we can’t go anywhere with Liv.” 

He comes around to sit on the bed next to her, “I took a day off and don’t worry about it,” He smiles before he gets up and walks out the door and she knows he disappears too quickly because he doesn’t want to leave room for her to protest. 

“Where are we going?” She calls after him. 

“If I tell you that it wouldn’t be a surprise!” Dean calls back, his voice faint. He’s probably already reached the living room with his long damn legs. 

  
  
  
  


*

  
  
  


Apparently, Dean already had his morning coffee. From the way he paces around, it also seems that he must have had a couple of cups too many. He left them to eat while he went down to see if Ash, Jody and Donna were alright. She wishes she could see Donna’s surprised face when the boss shows up at her workstation while the woman is nursing a hangover from last night. 

Afterward, he came up with a smile, which calms her because it means that everything’s alright with the three of her co-workers. With a clap of his hands, Dean gathers them at the door like a mother hen looking and checking that what they are wearing is alright for the day. 

“You excited?” He asks, his voice sounds awfully chipper. 

“No?” Y/N mumbles. She totally does not like surprises, given that the last one she got was Liv and even though the girl is the best thing that happened to her, still she doesn’t like surprises.

“I didn’t ask you,” He counters with his trademark smirk and looks to Liv, all bright smiles and crinkled eyes. 

“Yaaaaa!” The girl shouts. 

“Then let’s go!” He shouts back, equally cheerful.

Dean has bought a booster seat, or rather had let someone buy one for him, and has already fitted it into his tinted black SUV. He lifts the girl up and secures her in her seat. 

“I’m still not too sure about this.” She huffs out as she takes a seat next to Dean and reaches around her to buckle in her seatbelt. She can’t help but feel a little uneasy by the idea that they’re going to go away with the press still chasing them and Jimmy on the loose. 

He reaches out to take the hand that she has laid in her lap, gives her a reassuring squeeze, “Do you trust me?” 

Y/N looks at him and sees the little frown that’s on his face.  _ Does she trust him? _ Yeah, she has come to learn that she can trust him and she does.. But still..

She tries not to be a spoilsport and smirks tentatively, “I suppose, I do,”

His grin widens, his teeth showing, “That’s all I need,” 

Her mouth opens slightly, wanting to tell him that if he slips one time, that’s it, the trust won’t be there anymore but she thinks it wouldn’t be news to him. Dean’s not an idiot, clearly, he knows it, too.

  
  
  


*

  
  
  


The drive’s a long one. Olivia fell asleep twenty minutes ago, tired from all the bouncing she did because the little girl was just way too excited to get out of her  _ castle _ . 

Guilt seeps into Y/N’s mind. She can’t keep going like that, can she? She can’t keep Liv away from the world forever, especially not when there’s a wedding happening on Sunday. She’s an awful mother, she reckons, thinking she can lock up her child just because someone in her past tries to get to her. But that someone is Liv’s father, she’s going to do whatever it takes to protect her little girl. 

Perhaps, she thinks, it’s time to tell Dean. Time to tell him the reason why they can’t take Liv anywhere. Time to tell him the reason why Liv has to live a secluded life. Up until now, Dean thinks it’s because of the media, and he went along with it, didn’t question it. Only she knows that the reason is so much darker. Maybe, she’ll open up to him tonight, when the time is right. 

“You okay?” 

His voice booms next to her, jolting her back to reality and she swallows down the invisible lump of dread in her throat. 

“Huh?”

“I said your name three times, Y/N,” Dean looks over to her, tries to smile through his frown. He’s worried that she zoned out, she can see that.

“Yeah, sorry, I’m fine,” She mumbles, turning her eyes away from Dean to look ahead. Only now does she realize that they are driving through an empty parking lot of an amusement park. There aren’t any cars around but she’s sure that it’ll fill up soon enough. Wide eyed, she turns her attention back to Dean. “Dean, it’s an amusement park, what if people will notice you? What if they take pictures of Liv?”

She’s spiraling with the possibilities of how it will get back to her once the media catches so much of a glimpse of Olivia. Jimmy will never let her live it down and the thought scares her more than she cares to admit but before she can get to the worst case scenario in her mind, Dean reaches over, lays his hand on top of hers that is resting in her lap, picking nervously at the excess skin. 

“Hey,” His voice is soft and calming, the bass of it transfers over to her and strangely, it really does calm her. That’s how much of an effect he has on her, something she still tries to deny and bury deep within her so as not to get hurt, even if she knows that it’ll not work, “Don’t worry about it,” He goes on to say in that soothing voice of his and tries to smile, the crinkles deepen around his eyes, “I have rented the park for the day. There’s nobody else there. Every employee who’s on duty signed an NDA.”

“You did?” 

Now, the smile reaches his eyes and it’s crinkle city up there around it, “Yeah, I just wanted to offer Liv a great day.”

“Dean, you shouldn’t have spent money on us.”

The car comes to a halt right by the entrance to the park but they don’t get out yet. 

Dean twists his body to face her, “It’s the most fun way I’ve spent money in a long time,” and the smile he sends her is genuine. “C’mon, let’s wake up the princess,” He jerks his head to the backseat where Liv’s sleeping and she risks a glance, sees her child with her mouth hanging open, a little drool catches at the corner of her lips. Dean chuckles when he turns his head back from Liv to her, “Like mother like daughter,” He shrugs.

“Hey!” She snorts, her hand swats away at his arm and Dean laughs harder as he opens the door and gets out of the car.

  
  
  


*

  
  


It’s safe to say that Dean has hit the nail on the head with the day at the amusement park. Olivia is giddy, running ahead of them to get from one ride to the next, switching from the food stand, where she begged Dean to get her cotton candy, to the souvenir shop where he got her more tiaras and another dress that Liv insists on wearing right now.

While Liv runs ahead to get on the princess themed merry-go-round, they watch her go. She falls a little behind as Dean seems to be wanting to catch up to Liv. He’s more afraid of letting her unattended than she is. It’s adorable. He’s being good to them, there’s no doubt about that and knowing it, makes her heart soar. For the first time, she thinks that being married to him might not be such a bad thing after all, even though there are going to be doubts, but she has the feeling that she can make peace with it. 

He stops when he notices that she’s falling behind further, reaches out a hand that she happily takes. Dean’s quick to intertwine their fingers. His thumb caresses the back of her hand, drawing little circles as he pulls her along. She wraps her other hand around his arm, nuzzles her face into his shoulder and he tilts his head quickly, places a kiss on the top of her head. 

Y/N looks up, her chin still resting on his upper arm as they walk, “Thank you. It’s the happiest I’ve seen Liv in a long time,”

Dean smiles before inching down, and this time, he kisses her forehead. She likes them. Dean’s forehead kisses are phenomenal, they always manage to warm her heart. 

“Seeing her like that,” He looks ahead, his gaze is fixed on Liv. The girl waves at them and signals for them to catch up. Dean waves back before he tilts his head to her, “It was all worth it, you know?” 

“Still, you shouldn’t have,” 

“Y/N, I did it because I wanted to. I love to see her happy because you both deserve it.” 

She’s stricken by his words and she closes her eyes, feeling the tears pool behind her eyelids. She quickly blinks them away, trying not to think of life after Dean Winchester. The life that she left behind. The thought of returning to that life frightens her because it means that they have to let go of Dean who became a permanent fixture in their lives. In Olivia’s life. She maybe should have never let her into this life but again, seeing her child so happy and carefree, she thinks it’s worth it, too. They’ll get back on their feet, like they always do. Liv is resilient. The little girl helps build her up more than Y/N did for her and who is she to deny the girl that little shred of happiness before they have to go back?

He seems to sense her thoughts, because he stops and turns to her and when she opens her eyes again, she stares into the worried eyes of Dean. A tear escapes her, rolling down her cheek, even if she didn’t want it to. He studies her, seems to be able to read her mind and that’s the freaky thing he does. It scares her, but it also calms her at the same time.

His thumb comes up to brush at the stray tear, “You know that I’ll be here for Liv and you, right?” 

The tears start to sting again at his words, “How can you be so sure?” 

“I know you’re afraid,” Dean says, his hand cups her cheek, thumb brushing at another tear, “But I mean it, it’s not going to be over, and I do care for you. I care for Liv, I probably always will, and no matter what happens, I’ll always be here if you let me.” 

“Mommy!” The little girl’s voice pierces through the air. 

A smirk appears on Dean’s face, “C’mon, I think our presence is requested,” 

She nods as she let him guide her towards the merry-go-round, her hand in his. 

  
  
  


*

  
  


After the first rounds, Dean and Y/N got off and leaned against the railing to watch Liv going in circles.

“She’s a bundle of energy,” Dean moves closer, wraps an arm around her shoulder and she tilts her head to his, their nose almost touching. 

Y/N grins, “It’s the cotton candy you gave her.”

“That thing was almost bigger than her,” He laughs loud and sharp, “I’m sorry, I probably shouldn’t have gotten the biggest one.” 

“It’s okay,” She looks at her daughter when Liv calls out for them the moment she breezes past on her horse, “She’s happy, today is special.” 

“Yeah, she is,” Dean agrees. 

“She’s really looking forward to the roller coaster ride she’s allowed on next,” She adds. 

He groans next to her, dropping his head, “I knew it was coming when I brought her here.”

“Knew what?” 

“That I have to go on a roller coaster ride.”

“Dean,” She grins, showing her teeth, “Are you afraid of roller coasters?” 

“What?” Dean lifts his head to look at her. She can see that he’s trying to appear confident but there’s just something in his eyes, something she can’t possibly miss, “Nooooo,” He shakes his head vehemently, and adds, “I’m not,”

Y/N’s laughing now. Dean’s totally cute, he has no idea, “You totally are.”

“No? It’s just,” He starts to say and pauses dramatically, “You sit in a seat and then there’s nothing you can do about it,” 

She laughs a hearty laugh and Dean just stares at her. When she composes herself enough, she brushes a remnant of tears of her laughter away, “I’m sorry, I just hadn’t pegged you to be one to be scared of anything.” 

“‘M not scared,” He mumbles. 

  
  
  


*

  
  
  


Later, they are sitting on the roller coaster ride in the first carrier. Liv is to her right, a bright giddy smile plastered on her face, and yes, Dean’s to her left. The latter of them rubs his hand together and mutters pep talks to himself. 

As they wait for the ride to start, she places a hand on his thigh, “You okay?”

“Never been better,” He grits his teeth, his eyes not looking up. Instead, he keeps on staring to the place where her hand touches his jeans. 

“Dean,” Her voice is firm, wanting him to look up at her. It’s like she’s on a ride with two kids and frankly, the younger one doesn’t need her reassurance as much as the older one does. “Look at me,” He does, tentatively. His gaze screams panic and she feels bad, really bad. “Have you been on a roller coaster before?”

“No?” His voice is small, almost as if he’s ashamed of the fact, “Always avoided them like the plague.” 

“You know you don’t have to. You still can get off.”

“It’s okay, I promised Liv,”

They both look over to the hyper little girl whose smile never falters. Olivia shows them the thumbs-up, Dean returns it with a strained grin that doesn’t really reach his eyes.

When the carriage jerks forward, Dean spews curses under his breath, his hand grabbing at the handle of the ride, his knuckles turning white. She wants to say something encouraging, something that could calm him down but they are already on the way up. Liv screams of delight carry through the air while Dean has his eyes closed. She can swear she hears him humming something that sounds like a song from  _ Metallica _ . 

Since it’s still a kiddy ride, they don’t go as high up and when she opens her mouth to speak, her words come out of a scream as they descend with a fast tempo.

After the ride, she has to help Dean off his seat. His knees were wobbly and while Liv is ready to go on another ride, she tells her child to take it slow, to go get ice cream while she seats a pale Dean onto a bench right outside by the fountains and takes a seat next to him. 

“This is embarrassing,” He laughs but it sounds strained. 

“You’re only human, it’s okay.” Y/N sends him a smirk as she bumps her elbow to his arm. 

They both stare into the distance, watching Liv requesting an ice cream cone from the little parlor. The girl skips back after, careful not to drop her cone but Y/N can see that her daughter carries something else in her other hand. 

The girl comes close, stands right in front of Dean and hands him the can of ginger ale, “Here Dean, for you. Mommy always lets me have ginger ale when I’m pale.”

Dean smiles at her, lips curving up, teeth shining white, “Thank you, princess. You think it’ll help?”

“Only way to find out is if you drink it,” The girl shrugs before she takes a lick of her cone and giggles. 

Y/N heart almost bursts out of her chest as she watches them interact and she tries her best not to let her feelings overwhelm her. Crying for the third time since they’re here is definitely not a good look on her.

“You can sit out the next ride,” The girl says as she watches Dean open up the can and sipping on it. 

He almost snorts out the beverage when he hears it. Dean laughs, the color slowly returning to his face, “That’s awfully nice of you, princess.”

Olivia climbs onto the bench next to Dean and wraps her arms around his neck, the cone still in her hands but Dean doesn’t seem to mind, even if the ice could ruin his shirt. The little girl kisses Dean’s cheek and Dean stills. It’s the most affection Liv ever gave anyone apart from Y/N and Bobby. 

  
  
  


*

  
  
  


Later in the afternoon, Dean carries a tired Liv in his arms as they walk around the park. The little girl lays her head on his shoulder, seconds away from drifting off to sleep. 

“I think we should go home,” She says, smirking up at them. 

She notices Dean tensing before he swallows. She can see his Adam’s apple bob visibly.

“Yeah, we should,” He says and with his next breath, he adds, “Home.” 

“What’s wrong?” She narrows her eyes at him, wondering if she said something to upset him. 

“It’s just…” He starts but trails off, looking to the distance, to the exit that’s coming closer with each step they are taking. Dean shakes his head, lets out a chuckling snort before he clears his throat to speak again, “Home.. I like the sound of it. I never thought of my penthouse to be a  _ home _ . I guess,” He swallows again, “I guess it wasn’t one before you came along.”

Taken aback by his statement, she feels a flood of warmth inside her chest. She smiles as she looks up at him, sees his smile matching hers. 

“You’re lying, we made a mess out of your penthouse,” She snorts out a laugh and tries to swat at his arms but Dean turns away quick enough, trying to not disturb Liv’s slumber but he’s chuckling too. 

“Nah, I mean it,” He says with that playful smirk still on his face, “You and Olivia make it feel like home. Thank you.” Y/N looks down to her toes, feels somewhat flustered by his statement. Dean wraps his free arm around her shoulder, drawing her in closer and placing a kiss on the top of her head, before he whispers, “C’mon, let’s head home.”

  
  
  


_______________________________________________________

  
  
  
  


The drive home is quiet. Mainly because Y/N wanted to let Liv catch some sleep. Before they head into the city, she requests him to pull over and gently wakes Liv up again. Baiting the girl with some gummy bears, she says that the girl should wake up otherwise she won’t get any sleep that night. 

Dean stands leaning against the car, as he watches the mother-daughter duo do some exercises next to the car in order to get the girl awake enough so they can travel on without fearing Liv would fall asleep again. His face hurts from smiling so much while watching them. It reminds him of his childhood. At least the one when his mother was still alive. She did those things with him too. She would take him to places, she would build forts with him, she would read him stories. She made him happy. Until she was no more and his dad was all he had left. Suddenly, the laughter died down, the days got grimier, his schedule got tighter with education. The only person who kept him sane was Sam.

“Dean,” 

The voice jolts him back and he looks up to see Y/N holding Olivia’s hand.

“Huh?”

“We said we’re ready to head back,” 

“Yeah,” He sends them a smile, hoping they don’t notice how it doesn’t reach his eyes. He’s going to be okay, he knows that. Usually, he pushes the thought away, buries them deep in his mind, he doesn’t know why he let them surface today. 

  
  
  


*

  
  


They ate dinner together, and Dean uses the time where the girls occupied themselves between dinner and bedtime to go over some emails but it’s a mistake to do it in the living room while they were lazily watching TV because he can’t really concentrate but weirdly, he wants to stay here and not retreat into his study where he knows he’ll be alone. He somehow doesn’t want to leave this comfortable domestic bubble he found himself in.

The two girls are laying on the couch, Liv’s head in Y/N’s lap, a throw blanket thrown over her. The girl got into a bath before and she’s dressed in pj’s. It’s only a matter of time until she’ll fall asleep, Dean guesses.

After looking through the email, Dean doesn’t deem any of them important enough to answer now so he quickly abandons his laptop in favor of sitting down to watch a Disney movie with his two girls. 

_ His girls. _

God, it sounds awfully good in his head but he knows he shouldn’t let it slip out loud. 

He sits down next to Y/N, his arm draped over the back of the couch and she lets her head rest on his shoulder as they continue to watch.

It’s when the credit rolls that they realize that Olivia was sleeping soundly. Dean helps her carry Liv to bed and leaves her to do the rest while he retreats into the living room to clean up the toys the little girl hauled in there after dinner.

Dean picks up the toys and plushies, turns them in his hand with a grin but decides that he’ll just leave them all here. Maybe Liv will need them tomorrow, besides, he realizes that's the part where he said makes the penthouse feel more like home. 

Striding over to where he left his laptop, Dean grabs it and plants himself on the couch while he clicks through emails, thinking he could maybe answer one or two while Y/N puts Liv down.

“What are you up to?” The sound of her voice is right next to his head as she leans over the back of the couch. 

He chuckles, “Going through and answering my boring emails,” 

“I’m going to take a bath to unwind, will you still be here when I’m done?” 

Dean stares at the screen, tries not to let the image of her in the bath cloud his mind, “Most definitely,” He answers, fingers scrolling down the inbox that doesn’t seem to stop showing him unread mails. 

“‘K, I see you later,” She’s already past the threshold of the door but he seems reluctant to let her go. 

The next thing that slips his lips was unplanned, and maybe somewhat uncalled for, and Dean surprises himself with that. “Do you think I can join you?”

Y/N didn’t expect it either. He can tell when he looks back and sees her eyebrows rise on her forehead. But her face softens when she takes the next breath. Before Dean can talk himself out of it and tell her that it was meant as a joke, she smiles at him, “Yeah, I’d like that.” 

Instead of waiting for him, though, she walks towards her room and Dean needs time for the realization to settle that she indeed invited him to take a bath with her. What the fuck is he doing? He’s not even a bath guy. Hates it because it’s a waste of time. And yet, the thought of letting the day unwind in a warm bath with her sounds like a fucking good time to him. 

  
  
  


*

  
  
  


He shows up to her room with a bottle of wine and two glasses, figuring that if they are going to unwind, then they should do it right. 

The room’s empty, but the aroma of flowers lingers in the air. Dean walks to the bathroom, and sure enough, she’s already soaking in the bubble bath, not really waiting for him. A smile stretches on her face when her eyes notice what he’s carrying. 

Dean sets the wine and glasses on the ledge before he proceeds to take off his henley and sweats he changed into when they arrived home. Her eyes are trained on him, he knows, but since his back is turned on her, he does not so much see them as he  _ feels  _ them. 

And he’s right because when he drops his pants and turns around quickly in only his underwear, he catches her in the act. She has her lips between her teeth, the color rising on her cheeks as she finally looks away shyly.

He smiles smugly, tilts his head to the side and cocks his eyebrows, “You like what you see, sweetheart?”

_ Little shit. That’s him, alright.  _

Dean waits until her eyes hold his gaze at his remark before his thumbs hook into the elastic of his underwear. Without preamble, he pulls them down with one swift motion. 

He’s prepared for her to look away, because she’s a fucking good girl but when she doesn’t, he can’t lie that it throws him off. Just a little. 

Her grin widens on her face, the glint in her eyes full of mischief, “What if I say I do?”

Dean knows he should be ashamed of how his dick just twitches and hardens a little by her brazenness but he can’t find it in himself to care. His mind tries to come up with something to counter her but his mind stays blank, and now it’s his turn to get flustered. 

Wordlessly, he steps into the water that has way too many bubbles. He wishes it was less, so at least he would have her body to look at. Dean positions himself at the other end of the tub, doesn’t want to overstep boundaries. It’s a bath, nothing else, right? The tub is big enough to fit two people, even someone as big as he is. The bath in his room is much bigger, a total waste of space, since he never even used it but he let the interior designer talk him into it and he went along because they said that it would sell better if one day he’s going to move away. He doubts that would ever happen.

Y/N moves closer. Her legs touch his in the water and his heart picks up its pace, but she didn’t even get as far because she stops herself before she could get too close, pours wine into two glasses and hands him one. He swallows. Can’t lie that he feels a little disappointed that she keeps herself away from him.

They settle into their respective corners and start to talk about the day while sipping wine. At one point, her one foot creeps up his thigh. Dean catches it absent-mindedly and starts to massage it one handed. It’s when she stretches out her other foot to him that he realizes what he’s been doing. He chuckles and drops his glass to the ledge before taking her feet in both of his hands and starts to rub at them. “Are they hurting from walking around?”

“Yeah,” She sighs, “How about you? Anything hurt? You must be, from the way you were tense on the roller coaster,” A broad grin stretches over her face as she totally makes fun of him. 

“Hey!” He scoffs and starts to tickle her feet instead of massaging them. 

She places her own glass on the ledge and tries to scramble away, kicks at him but he’s holding a tight grip around her ankles. Laughter bubbles out of her mouth and Dean joins in. How can he not?

It’s when she notices that there’s no chance for her to win that she gives up. Dean braces himself for a counter attack but instead, she pats at the water in front of her. “Come here,”

He doesn’t know what it says about him that he goes in willingly without so much as raising an eyebrow. She places her hands on his shoulders, making him turn around, telling him to lean back into her while she spreads her legs to accommodate him. 

Leaning his head against her shoulder, she picks up the loofa Dean’s sure she bought herself, because he can’t imagine him having something like that in his penthouse since he’s not a bath person, and begins to soap him up with one hand while her other squeezes at his shoulder. For a girl, she has a tight grip. Her fingers dig right into his aching muscles. Dean has to suppress the sound his throat wants to push out. 

“God, you’re tense,” Y/N chuckles lightly, fingers working on the knots he didn’t even know were there, “‘S that from today?”

“From today and probably from the last five years.” He mumbles. It’s been quite a ride since he took over the company from his dad. His dad almost lost it, but Dean built it up, made it better. They came out of the ashes like a rising phoenix and are now stronger than ever before. 

“Mmh,” She hums as she continues to massage and stroke him. 

He gets hard from the touch, can’t really hide it, is thankful that there are still bubbles floating around to conceal it. 

“Is this what you wanted your life to be?” She asks out of the blue after a comfortable stretch of silence. 

“Uh,” Dean’s deep voice lingers in the air. He takes his time to think and then opens his mouth again to speak, “I never knew any different. The plan was laid out as far as I can remember.”

“Mmh,” She nods as if she understands. 

“What about you?”

“Well,” Y/N starts to say and even if Dean can’t see her face, he can tell that she’s grinning, “I certainly didn’t think I was going to be fake married to you.” 

Somehow the word  _ fake  _ hits him differently, he doesn’t even know why.

“What did you want your life to be if this didn’t happen?” He asks, after a silence that was a little awkward, not as comfortable as when they started out this talk. 

“I always wanted to get out of the city, buy a little house, watch Olivia climb a tree in the backyard, hear her giggles when she swings around on the tire swing.”

Dean smirks. He can picture the little girl doing just what Y/N told him when he closes his eyes. When he opens them up again he asks, “May I ask why you’re in the city when you want to get out?”

“Bobby,” 

“Bobby?”

“Yeah,” She exhales with a soft chuckle, “When I had nowhere to go, Bobby took me in. He’s here because of work and I kind of stayed because I found work too.”

“But you want to get out?”

“Someday,” She agrees, “I want to work to save up enough money for a house,”

He rubs a hand over her knee that she has propped up next to his body. He almost says that he would buy her one but he knows that she won’t take what he offers. She’s independent and that is a fucking pain in his ass sometimes. 

“Apple pie life,” He says. 

“What?” 

“Yeah, that’s what you’re dreaming of, huh? White picket fences, a car, a house with a big yard, a dog, 2.5 kids,” 

Y/N starts to laugh, he can feel her chest moving behind his back, her soft tits bounce, skin on skin, “Well, I would appreciate it if you don’t call my child a  _ point five _ , but yeah, something like that.”

Dean has to grin, but then his voice turns somber. “Why did you say you had nowhere to go?”

“What?”

“Yeah, you said before Bobby took you in when you had nowhere else to go.”

He feels her inhaling sharply. 

It’s a long pause and Dean grips her knee one handed, strokes her softly, his thumb painting circles on her skin as he waits. He has all the time in the world and he’s not going to ask again and pressure her.

When she speaks again, her voice is soft, he has to strain to hear it. 

“Olivia’s father and I didn’t part on good terms. I think I mentioned that before,” Her voice is a little shaky, “I kind of took her and left before I even thought about where I could go. The only person in my life who would be willing to take us in was Bobby.”

“He’s a good man.” 

“The best.”

“I’m sorry for what happened,” Dean says genuinely, apologizing for things he had no control over. It just felt like the right thing to say, also because he doesn’t know what else he could be saying to make it better for her.

“It’s okay, it’s in the past.”

He thinks he has to change the subject, he doesn’t want the evening to end on a grim note. So he opens his mouth to speak, “Have you thought about having Liv in the wedding? As a flower girl or something?”

She snorts, “I can’t do that.”

“Why not?”

There’s a pause and her fingers dig deeper into his shoulder. Dean’s aware that she doesn’t know that he already knows and Dean’s not really pressuring her. He wants her to talk about it when she’s ready. 

Tonight seems to be the night because after what he thinks is a silence for her inner debate, she exhales, “Jimmy. That’s the name of Liv’s father,” She starts, and after a beat, she adds, “He, uh, he said he wants to take Liv away from me. I don’t want him to see her face in the media, don’t really want to give him any leverage over me.”

In a matter of seconds, Dean manages to manhandle her around so his back is against the tub and she’s on top of him. He figures it won’t be a problem since his hardness has subsided but feeling her weight on top of him, his dick betrays him and starts to stir. He ignores it while he cradles her in his arms. His hands stroke her back and he brushes a strand of hair behind her ear while she leans her face on the side of his chest. All the fight has left her, she’s too tired to even say something about the way he places her on his lap.

“I know about Jimmy.” His voice is soft, almost as if she doesn’t want to scare her away with his revelation. 

Tilting her head up to him, she frowns, her eyebrows knit together tightly, “You do?” 

Somehow, he’s curious why it doesn’t surprise her but thinks it has something to do with how he always wants to have control over every aspect of his life.

Dean nods his head, “Yeah, he tried to blackmail me,”

“Ugh,” She groans and rolls her eyes, her hand goes to his chest as she tries to push herself up, but Dean doesn’t let her. Instead, he keeps on holding her close to his body. She starts to mumble, “I’m sorry, I told him that he’ll get what he wants but he has to give me time. He should never have contacted you. That’s not what I wanted. I can understand if you don’t want to go forward with the marria—”

“—Who says I don’t want to?” Dean cuts in, his voice a little louder than intended but he’s just so irritated that she thinks little shit like Jimmy would throw him off.

“Well, I thought, you know,” Y/N shrugs.

He waits but she doesn’t seem to know how to continue. So he speaks, “I’ve talked to Jimmy.” Her eyes widen, her lips form an O and then she gasps like she wants to say something. Before she can, Dean cuts in, “Made a deal with him.”

She looks at him, and the frown is there again, “May I ask what the deal’s about?”

“If I tell you I’d have to kill you,” He lightens the mood with a joke and it works because she’s smirking before she rolls her eyes dramatically. 

“I didn’t want you to spend money on my problems.” 

Dean shrugs, “We’re going to be married. Your problems are my problems. And besides,” He grins cockily, “He really has no business skills whatsoever so it was quite easy to get what I wanted.”

“What did you want?” She asks, pulling her lip between her teeth, and Dean just really wants to kiss them.

“For him to leave you alone. Leave Liv alone.”

“How much did you pay him?”

“Not as much as he wanted because I have better people to dig around. Did you know that he got married after you left him?”

From the way she flinches, he takes it that she didn’t know.

“How do you know?” She asks.

“I have people help me dig around,” He shrugs to which she cocks one eyebrow. He goes on, not elaborating on his  _ people _ , “He was in jail for domestic abuse once so I gave him an ultimatum. His ugly face won’t get dragged by the media when he agrees to sign an agreement that says that he’ll stay away for good.” 

Dean’s actually afraid of her reaction to him meddling in a part of her life he has no right to but by the way her smile stretches over her face, he probably has no reason to doubt that what he did was the right thing. 

“Thank you,” She says shyly, and adds, “But I could have held my own.”

“I have no doubt about that,” He agrees, his tongue comes out to wet his lips, “But sometimes, you should let people help you so you have enough energy to be strong for Olivia. Did Jimmy ever lay a hand on you, on Liv?”

He can’t really explain his curiosity, but what he knows is that he’s holding his breath waiting for an answer.

“Only me, once. That’s when I packed and left.”

Dean’s jaw starts to tick and he swallows the urge to go and find the fucker, maybe rip him a new gaping hole.

Y/N tilts her head up to him, places a kiss on his jaw and smiles softly when his beard pricks her lips. Strangely, it manages to calm him down. They stay like that for a while longer, neither of them saying a word. They don’t need it, and Dean’s sure that she can feel how much tighter he’s holding her, letting her know wordlessly that he won’t let things like that happen to her ever again. 

Dean also thinks that even though they’ve seen each other naked before, and even had sex, still, this is the most intimate he’s ever been with anyone. Just them together, in a bathtub full of water, touching but not really touching. 

He only notices that the water runs cold when she shivers in his embrace. “C’mon,” Dean presses a kiss on the top of her head, “Let's get you out of the cold water and into a warm bed.”


	22. Chapter 22

“Mmh,” Dean hums in delight, the corner of his lips twitch, a grin tugging on the edge until his mouth stretches wide.

It’s a dream. A fucking good one, and Y/N’s in it. 

The stretch of her lips matches his as she hovers over him, her hair cascading down, tickling him, and she whispers something in his ear. He can’t quite make out what she says but it makes his heart beat faster nonetheless.

_ Dean _ .. 

His name sounds featherlight when it spills from her lips, warming up his insides. Little kisses are pressed onto his jaw. Her scent wraps around him and he inhales deeply, not wanting to wake up ever again if  _ this  _ is his dream. And if this is his state of dying, he reckons, it’s the best way to go.

He’s asleep, at least he’s fairly sure of that, because he’s dreaming of nimble fingers stroking him, he’s dreaming of velvety soft tongue licking up his shaft tickling at his leaking slit. Soft lips sealing around the bulbous head before the slick warmth engulf his now hard cock. 

Dean barely registers the warmth of the sheets he’s pressed into, barely registers the softness of the pillow that supports his head because all he feels is  _ bliss _ . He doesn’t think there’s another word for it.

After a while, she stops bobbing her head and kisses down his lengths to worry at his balls. Sucking them in one by one while her small hands grip his cock tight, stroking the skin up and down wetly. 

_ God _ , Dean really does not want to wake up in fear that this is all just what it is - a dream.

_ Dean..  _

_ Dean.. _

The sound of her voice gets louder, the suckling on his balls has stopped and he feels her hot breath against his shaft as she calls out his name. 

_ Nope _ , not going to wake up. 

There’s the feeling of her fingers cupping the fluff of hair on the base of his dick, fingertips brushing against his pelvis as they move up to his stomach, nails raking along his skin, tickling him a little, making him shiver slightly.

He fights with himself not to wake up as his grin widens when he feels her hot wet mouth going back to his cock.

_ Nope. Not happening. _

Dean lets himself dream the best of dreams in existence, his hips buckle up unconsciously at the feeling. There’s the sound of her choking when the tip of his dick hits the back of her throat. Far away, there’s a cough, and the warmth around his dick is gone. 

_ No, no, no. Please.  _ He wants to say but fearing if he does, this will all go away.

With his eyes still closed, he reaches downwards with both his hands, frowns when his fingers intertwine with hair because dreams shouldn’t feel so real.

Reluctantly, Dean squints his eyes open. He blinks the sleep away and pulls his hand back from her to rub at them. It’s still dark out, if he has to guess, he’d say that the day is about to start. The lights spilling in from the window illuminates her features. When he’s sure enough that this is indeed not a fucking dream, nor a fata morgana, his smile widens. 

“Y/N?” His voice is gravelly, right when he wakes up, it usually is deeper than it normally is. But maybe the sound of his voice also has something to do with his hard cock being sucked by her. At the mention of her name, their eyes meet and she pops the tip of his cock out of her mouth with a lewd and loud pop. slurping up the excess slick that drips around the corner of her mouth.  _ Jesus fucking Christ _ , she is a fucking filthy dream. “What are you doing?” He asks when his brain is back to being able to think straight.

She licks a stripe up his shaft, her tongue darts out to swipe at her wet lips before they stretch across her face into a grin that tells him that she’s absolutely up to no good. Not that he minds.  _ God _ , he so wishes he could capture the sight, but that’s not possible so he commits it to memory instead.

“‘M waking you up,” She looks up at him innocently, though her grin is anything but. Darting her tongue out, she twirls it around the leaking head of his dick, pulls her face back and there’s a faint string that connects her tongue to his slit. Dean groans out audibly at the sight. “‘S that okay?”

_ Fuck. _

Dean props himself on his forearms to get a better look. He can not  _ not  _ look. He swallows hard before he tries to speak, “Better than okay,”

Y/N breathes out a smile, her hot breath hitting him the right way, and then she’s on him again, sucks and licks at him like he’s the best goddamn lollipop. He can’t help it, his one hand goes to her face, tucks a loose strand of hair behind her ear, leaves his hand spanned wide on the side of her head, not really forcing her or anything, just resting, somehow he feels the need to be connected.

“Mmhh,” He hums, “That’s good. Just like that, baby,” His tongue darts out to wet his own lips, the tip of it resting at the corner of his mouth, “Your mouth feels so fucking good. Sucking my cock like a good girl, don’t you, yeah?”

She’s moaning at the praise, sending vibrations down his lengths, and one thing is for certain, he’ll never ever stop praising her. The other thing that’s for certain is that he’s sure she’s actively trying to kill him, waking him up like that. 

Her one hand massages his balls, twirls them around as she sucks his dick. His fingertips curl into her hair, grabbing a hold at it as she bobs her head rhythmically. 

“Jesus fuck, Y/N,” He pants, chest heaving, and the other curse words get logged in his throat. It needs every ounce of his self-control not to fuck up into her warm mouth.

It seems like the misery at the way he’s trying to hold himself back just makes her want to torment him further. Her lips are around his cock, sucking harder than before as her head bobs. She’s gobbling him down in the best way and he absolutely doesn’t mind it. It’s just hard to hold himself back. What she can’t swallow down, she works with her tiny nimble hands while she rolls his balls in her palm with her other hand.

_ Goddammit.  _ Dean’s a fucking second away from spilling.

The functioning brain cells manage to get him to speak, manages to warn her, albeit it comes out very quietly and it’s more of a jumbling of mumbles than words, “Baby, I’m gonna come, fuck,” Is what he says but he has no idea how it came out.

She pops his dick out and he nearly weeps at the loss. However, he’s rewarded with a grin that screams  _ mischief _ and there’s amusement in her eyes, “Come in my mouth,”

Dean doesn’t even get a chance to add anything to that because she’s quick to take him again, strokes him faster too and he doesn’t fucking know how she knows how he likes it but she does and  _ shit _ . His orgasm hits him square in the chest, he arches off the mattress, buckles his hips as his legs tremble. He’s so fucking glad he’s not standing because his knees would definitely give out if he was.

Y/N coughs when it’s too much to swallow, Dean watches the cum dripping out of the corner of her mouth and down his shaft. She regains her composure pretty quick, though, swallows the cum that she can and proceeds to clean up his shaft and pelvis by licking him up, like the good fucking girl she is. His heart fucking swells as he watches her and he can’t believe that this is not all a dream. 

She gives his softening dick a last gentle kiss before she climbs up his body. Dean tugs her towards him, grabs her by the back of her neck to pull her into a frenzy kiss and groans when he tastes himself off her tongue. He swallows the sounds she makes greedily. 

He has to break the kiss for air, is still too fucking exhausted from how hard he came. “I could get used to getting woken up like this.”

Chuckling, she swats his chest, “Don’t get used to it.”

“What time is it?”

She plants herself next to him and Dean tucks her under his arm, letting her rest her head on his shoulder. He wonders if he has time to return the favor, maybe coming inside of her too, because Lord knows he can not fucking get enough of that.

“It’s almost 7 AM.”

“What?” It comes out louder than he intended but he’s not really mad, he’s just surprised. He notices how she flinches in his grip. Dean draws circles on the skin of her arm with his thumb.

“Yeah, I heard the alarm and you actually reached out to silence it but then you fell back to sleep, and apparently, so did I,” She mumbles next to him. Dean can hear that her voice is already laced with fatigue again. Yawning, she smacks her lips before she continues, “When I woke up again, it was way past 6.30 AM and I thought I have to find a way to effectively wake you up.”

Dean chuckles lightly.  _ That  _ she definitely did.

He looks down at her, places a kiss on the top of her head and she’s yawning again. He wants to stay here a little longer, wants to fall asleep again, maybe wake up later, eat her out instead of breakfast but before he can make himself cozier, she rolls away from him and turns the other way. He chases her, rubs his beard on her naked shoulder, plants a kiss and drives his fangs in. She chuckles in amusement. 

“Go, Dean. You’ll be late.”

“I don’t wanna,” He drops his forehead to her naked shoulder.

Y/N reaches back, curls her hand around his neck, and pats the back of it, “There, there. Big CEO doesn’t wanna face the day.” 

Well, she’s not wrong. He really should get up. There’s no time to waste and if he would stay, it would definitely not be easier.

“I’ll make it up to you,” He presses a wet kiss to the back of her neck and rolls the other way. 

When he gets up and slips into his sweatpants, she squints her eyes at him, “Make up for what?”

“Oh you know,” He shrugs with his signature grin as he picks up his shirt from the chair he moved there last night after tucking her into bed and cleaning the bathtub. Chugging the shirt over his head, he sees her grinning back at him. 

“No, it was actually a thank you from me.”

Dean walks over to the nightstand and grabs his phone, “‘S that how you thank someone, huh?”

“You have a problem with that?” How her eyes can look at him challenging when they’re only half open is a miracle to him. 

“Not one damn problem.” He places a kiss on her forehead, by now it’s out of habit but she doesn’t seem to mind so he doesn’t either. 

  
  
  


_______________________________________________________

  
  
  


At 4 PM, when Liv was baking something with Missouri, Y/N’s phone buzzes and she takes it out of the back pocket of her jeans.

> _ D: I should definitely not tell you this but ambush on the way. Donna asked me to get off work earlier. I think they want to take you out. _
> 
> _ Y/N: And you allowed it? _
> 
> _ D: I’m a cool boss. _

  
  


She groans and before she can even pack her phone away, the doorbell rings. 

  
  
  


*

  
  


It’s the first time Donna’s in her bedroom and the blonde rifles through her closet. Apparently, she already talked to Missouri about kidnapping Y/N and Missouri agreed to stay with Liv until Dean or Bobby would be back. Y/N’s not entirely sure if that’s a good thing that they’ve all planned it behind her back. 

“Oh my god, so much lingerie!” Donna exclaimed, holding out a set of pastel pink lingerie in lace. 

Y/N walks out of the bathroom, her skin’s still damp and her hair wet, “More than I can wear,” 

Donna picks out a dress, it’s pale yellow, she thinks it’s a new one. She lost track of all the dresses and clothes because Garth keeps on sending her new ones. Y/N isn’t even sure if Dean knows about it. 

“You sure I can borrow this?” The blonde asks, holding it up to her body and marvels at her mirror image.

“Suit yourself,” She shrugs with a smile, “It’s not like they’re mine.” 

Her friend has chosen a dress for her as well, something white, and Y/N’s not sure if it’s the right choice because she’s a klutz and white things don’t always stay white. This will probably be a super pain in the ass at her rehearsal dinner and wedding. She’ll have stains all over it. Eh, not that she should care, right?

Y/N takes her time saying goodbye to Liv and when she stands in the elevator with her friend, Donna still wouldn’t tell her where they’re going. 

“C’mon!” She demands, her voice comes out a little whiny.

“It’s a surprise!” Donna giggles. 

“I hate surprises.”

“It’s going to be fine, Y/N. It’s your bachelorette party, we’re going to have fun!”

“No strippers, Donna!” 

The woman’s jaw drops when she lets out a gasp in faux irritation, “How dare you think I would hire a stripper when you have Dean!”

Y/N can’t really hide her smirk. 

“Garth is volunteering to strip for us,” Donna mutters under her breath as they both step out of the elevator and Y/N nearly doubles over from laughter.

They walk out of the building and she watches as her friend leads her to a waiting limousine instead of the usual Uber. 

“All fancy, aren’t you?” She asks with a glint of amusement in her eyes. Donna really goes all out and she’ll have to make sure to repay her friend when it’s her turn to get married.

“Your fiancé won’t let us take an Uber,” The blonde shrugs and when they near the car, the driver gets out to open the door for them.

“Of course he doesn’t.” Her eyes roll to the back of her head. “He’s a worry-wart.” 

“He’s great,” Donna chirps as she gets in. 

Y/N lets herself fall into the limo and waits until the driver closes the door before she lets out a loud sigh, “Try controlling and patronizing,”

The other woman snorts, hand reaching out to grab at the bottle of Champagne that’s been sitting chilled in a cooler before turning to her, “That’s his nature, isn’t it?”

“Yeah,” She mumbles, and adds with a firmer voice, “He doesn’t like me taking an Uber, apparently.”

Donna’s hand working on the wrapping on the neck of the bottle, “As he should. You’re his fiancée. What if someone kidnaps you?”

With wide eyes, Y/N looks at her friend. The thought never crossed her mind. “You think it would happen?”

“You’re going to get married to one of the richest bachelors of the modern business world, so yeah, I think it’s a possibility.” 

The cork plops open with Donna’s giggle and the woman’s quick to fill up two glasses, handing one out to her which she takes. They clinked their glasses and she drained it in one go. Maybe Donna has a point. She just never saw that point. It seems like she has to adjust more than she thought she would have. 

The drive is a long one and every time Y/N asks Donna where they’re going, the woman wouldn’t budge and spoil the surprise. So she settles into sitting back and talks with her friend about all the things they have missed talking about.

Y/N fills Donna in on the day at the amusement park, the eyes of her friend are as big as saucers when she recounts how Dean fucking Winchester paid to rent out a freaking park for a day. The woman smiles warmly when Y/N tells her about the bond he has with Liv. 

“That’s huge, Y/N,” Donna states, and somehow there’s nothing but admiration in her tone of voice. 

“I know.  _ So huge _ . Olivia likes him so much.”

“Knowing her, she probably has him wrapped around her tiny little fingers,” The blonde takes a swig from her flute. 

“Oh, no doubt about it. It doesn’t seem like Dean’s not comfortable with it, though. You know I wouldn’t spring Olivia on him if he wouldn’t be comfortable, in fact, I tried to keep them apart but Dean insists that it’s okay and he likes her. Apparently, she likes him too. This will be so bad when we go back to our lives.”

Her friend almost chokes on a mouthful of champagne and Y/N rubs over Donna’s back while the woman pumps her fist against her chest.

“Are you okay?” Y/N asks, palm smoothing over her friend’s shoulder and down her back. 

“Yeah,” Donna chokes out, “I thought I heard you talking about going back to your life.”

“Donna,” She says sternly.

The blonde empties her glass before setting it down, “Look, Y/N, I’m just saying, from the look of it, there’s no way he’d let you go back to your old life. And why would you want that anyway? You and Liv, you both deserve something good.”

Y/N looks away and out the window. She has noticed that they’re leaving the highrises behind. “Maybe we do but I don’t think it’s going to be with Dean.”

“Why?” Her friend asks, “You guys get along so well. He really cares for you, as far as I can see, and he’s able to provide for you, for Liv.”

She shakes her head, her breath comes out a sigh, “Money is not everything, Donna. Maybe it won’t work because I’m longing for something money can’t buy.”

The tension in the car is palpable and Donna shifts closer, her one hand still holding the now second champagne bottle as she nudges her shoulder against Y/N’s. “You’re falling for him, aren't you?”

Happily accepting the flute that Donna filled to the brim, Y/N leans back in her seat now, sighing as she goes, “I’m in so deep, Donna. I didn’t want to and I tried to fight it but it was not possible.”

“It’s inevitable,” A sly grin creeps on the blonde’s face, “I’m not surprised.”

She empties the flute in one go, feels the buzz of the alcohol slowly taking over her mind, “I think I’m falling in love with him.”

“What’s so bad about it?” Donna asks, seemingly clueless but then something clicks and her voice gets soft, “You’re afraid he's not going to fall in love with you too,”

“I  _ know  _ he’s not going to fall in love with me.” She huffs out, “And you know, I knew it. He told me,”

“He told you?”

“He told me at the beginning that he’ll never be able to love me.”

“Wow, that’s harsh.”

“Yeah,” Y/N snorts, somehow trying to play it cool, “But whatever. I know that, and it’s better to know it beforehand, right?”

Donna’s looking at her with a frown. 

“I’m okay, Donna, don’t worry. I had time to prepare myself. It's just..” She starts and trails off, taking the bottle from her friend’s grip and takes a large gulp straight from the bottle.

“You don’t want to tell him, do you?”

“Nah,” She shakes her head, denying it as best she can, “At least not for the time being.”

“God, Y/N, this is fucked up.”

Y/N snorts out a chuckle. It really is.

The limousine comes to a halt before Donna can ask her more and she’s kind of glad. They get out and immediately a breeze ruffles through her hair. It carries a tint of salt with it. Turning around, her eyes catch the pier and the restaurant next to it. Fairy lights lit up the terrace overlooking the ocean. 

“It’s beautiful,” She says and Donna’s smile stretches across her face. 

“Garth works here,” Is her friend’s answer. “He got us the best table and there’s bottomless Sangria.”

“Of course,” Y/N shakes her head in amusement as she hooks her arm into Donna’s as they make their way up the short step. 

Their friends are already waiting and she’s super glad Donna opted for a quiet meal with friends instead of going clubbing for her bachelorette party. 

  
  
  
  


*

  
  
  


They sit and laugh, listening to Ash recount the bar brawl that Dean had started. Everyone was laughing and maybe, she thinks, maybe it has something to do with bottomless Sangria because her head’s swimming too. She was not even surprised, nor did she care to hear that the wedding announcement in the papers was so huge, Jody choked on her morning coffee while she read it.

As it gets darker, the fairy lights really did the deed, illuminating the place enough to create a warm and loving atmosphere. 

“I love it here,” She whispers into Donna’s ear, “And I love you.” Her speech is slurring a little and then she grabs at the closest person next to her, plants a kiss right on Ash’s cheek, “And I love you. I love everyone.” 

They start to laugh. 

“You’re drunk, Y/N?” Ash asks as she gets up to hug each and everyone who showed up, staggering a little on her heels. 

“Nah,” She says, a hiccup escapes her and she knows her word is a lie.

They have to help her sit down again so as to not let her fall flat on her face. 

  
  
  


_______________________________________________________

  
  
  


Dean slips soundlessly into the penthouse, after having dinner with Sam. He figured if Y/N went out, there’s no use for him to stay home either, especially when Liv would be sleeping anyway and there’s nobody to keep him company. He’s really just not used to being alone with his thoughts anymore and kind of misses the life in the penthouse that the two girls brought when they moved in.

As soon as he changes into a shirt and sweats, his phone vibrates where he dropped it on the bed. 

The name that flashes on the screen is a known one but one he didn’t expect to be calling at this time of the night. 

“Donna?” He practically shouts in the receiver as he leaps onto his feet, his heart picks up its beating, his breath is quick and shallow. There are thoughts popping up in his head that something happened to Y/N and he can’t quite shake it out of his mind, “Is Y/N okay?”

After he says it, he holds his breath. 

“Y/N? Oh yeah, she’s definitely okay,” Donna chuckles. In the background, Dean hears a giggle that clearly belongs to Y/N. He feels the tension draining from his body. “I just want you to know that we’ll be at the building in about ten minutes.” 

“Okay?”

“Yeah,” Donna says and Y/N giggles some more in the back, “I don’t think she can get up there herself,” 

“Don’t worry, I’ll come meet you,” Dean’s answer comes out immediately.

Dean’s sitting on the steps leading up to his office building in his cap and a sweater pulled tight. There’s no photographer tonight, they’re probably already sick of him not showing up all the time. 

He jumps up when he spots the limousine, jogs to the curb and cracks the door open. Y/N is bleary eyed but there’s a smile.

“Hi fiancée!” Her speech slurs but it’s bright and when she smiles, he can see all her teeth. He has to chuckle to himself and holds out a hand to help her up. 

Y/N lays her hand in his, lets him pull her out of the car and staggering right against his chest with a laugh. 

Meanwhile, the driver rounds up to them, closing the door for him. He says bye to Donna and tells the driver to drop her home safely. Y/N distracts him from talking for a moment when she buries her face into the crook of her neck and sucks on his skin there. 

He stands a little straighter, with her still tucked into his side as he watches the car drive off before turning to her. Her eyes are hooded, but she’s still wearing that smug grin only a drunk girl can wear, “Y/N, are you drunk by any chance?”

“Me?” She gasps and places the palm of her hand to her heart, feigning hurt. It’s totally adorable. “Never!”

“Right,” Dean nods his head in agreement, a grin stretches across his face. “So, you’re okay on walking into the building yourself?”

She snorts as if he offended her and starts to walk away from him. Dean crosses his arms over his chest as he takes in the drunken form of her. It’s like watching a fawn taking its first step. After about three full steps, she turns around and fucking pouts.  _ God _ , he can never resist that fucking pout. Her hand fits in her dress, almost lifting it up enough for him to see her underwear and it’s super great that there’s nobody around here in this time of night. 

“You want something, sweetheart?” The words leave his mouth too smugly. 

He watches her take a deep breath before she rolls her eyes back to her head. It needs everything in him not to burst out laughing. 

“Fine,” She sighs, “Can you help me? Please?”

Dean debates teasing her a little longer but he thinks it would just not really be fair when she can’t fight back so the only thing he says is “Of course,” before he scoops her up into his arms bridal style and carries her inside. 

Her arms loop around his neck, face burying into it, rubbing against him like a damn cat in heat. 

“Thank you,” She mumbles so softly he almost didn’t hear it. 

“You’re welcome, baby,” He answers, pressing a soft kiss on the top of her hair as the elevator rides up to their home.

Getting her into bed is a challenge on its own and Dean honestly never thought that he will ever have to experience it. If someone would have told him a couple of weeks back that he’ll be holding a girl’s hair back while she empties her stomach into a toilet bowl at one point in his life, he’d say they’re crazy. Yet, here he is, maneuvers her over to her sink and brushes her teeth. He just hopes they are quiet enough because he wouldn’t want to wake Olivia. He doesn’t think he can deal with getting a child back into bed too when he has his hand full with the child’s mother. He’s just not that experienced yet, but he sure as hell is learning.

Instead of laying her right down on her bed, he sets her on the edge, “Stay here,” He warns her. Thinks it’s stupid because she obviously is in no shape to get away but whatever.

Quickly he darts out of the room and comes back with water and Tylenol. He makes her take two, watches until she downs the whole content of the water bottle.

Y/N gets up from the bed, still on wobbly feet.

“What are you doing?” He asks her, hands curling around her wrist while his other hand slides around her waist to help hold her steady.

“I need to pee!” It comes out a mixture of a hiss and murmur. 

“Oh,” He says and lets her go but he’s still holding his hands up so that he could reach out in time should she fall. And then, he watches her go, with a reminder, “Keep the door open.” 

“I will not do that!” This time, it comes out as a real loud hiss. 

It’s torture not knowing if she’s doing okay in there. But he hears the flush of the toilet, so at least there’s that. And after a while, he hears the water running. No sound of a bang of her head on something, he takes that as a win.

The door opens as Y/N leans against the door frame, her forehead resting on the wood. It looks like she’s struggling with keeping her head up. It must feel like a ton. He knows that feeling too well. 

“Dean?” His name leaves her lips and it sounds good coming out all whiny and cute. It’s probably second on the list of how his name is called out, right after how it sounds when she calls his name when she comes. 

Chuckling, he steps in front of her and places her arms around his neck, “Hold on,” He whispers, “I got you,” 

Scooping her up into his arms, he carries her over to her bed and lays her inside. Her hold around his neck is still tight, not wanting to let him go but he has to because there’s still the dress he has to get off her. He pulls himself away enough but she whines at the loss of his body heat. 

The dress is off quick and she isn’t wearing a bra, so one less thing to take off, which is better for him, but also it’s really not good because he’s kind of half hard just seeing her tits. He pulls the comforter over her body, tucking her in. She literally purrs after she has made herself comfortable. His hand cups her face before he strokes her hair back on her head. 

“Good night, sweetheart,” He whispers, can’t help but lean down to place a kiss on her forehead before retreating. 

Turning around, he’s ready to leave but before he can even take a step away from the bed, her hand comes up to tug at his wrist.

“Stay?”

He looks back at her, her hand now back below the pillow as she closes her eyes. She’s so sure that he’ll stay because there’s no doubt on her face as she lets herself fall into a content state of mind before falling asleep. And who is he kidding, he’s not able to say no anyway. Wordlessly, he removes his sweatpants and sweatshirt, walks around the bed to get in behind her and pulls her into his chest, his arm around her waist while he nuzzles his nose into her neck from behind. The sweet scent of alcohol mixes with her own. It’s quite intoxicating.

“Did you have fun?” He asks, not particularly knowing if she’s already asleep or not because her breathing has slowed down since he pulled her into his arms.

“Mmh,” She hums in agreement.

“Mmh?” 

“Donna is great. I love her.” Y/N mumbles, “I love Jody too, love Garth, love Ash,” She’s slurring and her voice sounds so far away. She’s slowly drifting off, he can feel by the way her hand that she placed on his that’s resting on her stomach drops down to the mattress. 

“That’s good,” He whispers as he places a kiss behind her ear. 

“Mmh,” It comes out laced with sleep. “Love you, Dean.” 

Immediately, his body goes rigid while his heart runs a marathon.

**Notes for the Chapter:**

> Oh no! What will happen now? ;)
> 
> Come find me on tumblr @smol-and-grumpy <3


End file.
